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Mahrwald, R.; Schetter, B., Science of Synthesis, (2008) 36, 936.
Aldol reactions between trichlorosilyl enolates and aldehydes were described for the first time in 1996.[538] In contrast to the well-established Mukaiyama reaction, in which Lewis acids are deployed, this transformation is catalyzed by Lewis bases. The aldol adducts are obtained with a high degree of enantioselectivity and this endeavor, which is strongly connected to the development of an easy and general protocol for the synthesis of trichlorosilyl enolates and chiral Lewis bases, has been comprehensively reviewed.[539–541] As a result of these studies, trichlorosilylated enolates of carbonyl compounds can be obtained by metal exchange reactions either between the corresponding enol stannanes of ketones and silicon tetrachloride, or between trimethylsilyl enol ethers and silicon tetrachloride in the presence of catalytic amounts of mercury(II) or tin(IV) salts, or palladium(II) acetate.[542] For example, the syntheses of the trichlorosilyl enolates of aldehydes can be accomplished by transmetalation of the corresponding trimethylsilyl ethers with silicon tetrachloride in the presence of catalytic amounts of palladium(II) acetate.[543,544] Once formed, the trichlorosilyl enolates 313 of ketones react with aldehydes without any activation to give the corresponding β-hydroxy ketones 314 in high yields after 4–10 hours in dichloromethane at room temperature (Scheme 125).[545]
Meeeee 888 Meeeeeeeeee Meeee Meeeeeeee ee Meeeeeeeeeeeee Meeeeeee ee Meee Meeeeeeeeee[888]
| M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|
| Me | Me | 88 | [888] |
| Me | Me | 88 | [888] |
| Me | Me | 88 | [888] |
| Me | Me | 88 | [888] |
| eMe | Me | 88 | [888] |
Me e eeeeeeee eeeeeee eeeeeeeeeee eee eee eeeeeeeeeeeeee eeee eeeee 888 ee eeeee-8-eee eeee eeeeee ee ee eeeee eeeeeee eee eeeeeeee; eeeeeee, eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee eeeee e eeee eeeeeeeeeeee eeeeeeeeeeeeee.[888] Me eeee, eeee eeeeee eeeee eee eee eee e eeeeeeeeeeeeeeee eeeeeee ee eeee eeee ee eeeeeeee, ee eeee eeeeeeeee eeeeeee eee eeeeeeeeeeeeee eeee eeeee ee eeeee-8-eee eee eeeeeeeeeeee ee eee eeeeeeee ee e eeeeee eeeeeee-eeeeeee eeeeeeeeeeeee (eeee ee 888, 888, 888, ee 888) eee e eeeeeeee eeeeeeeeeee ee −88°M eeee eee eeeeeee eeeeee 888 eee eee eeeeeeeeee ee eeeeeee eeeeee (eee eeee eeeeeee eeeee eeeeeeee eeee eee eeeeeeeeeeeee 888) (Meeeee 888).[888]
Meeeee 888 Meeeee Meeeeeeeeeeeee ee Meeeeeeee ee Meeeeeeeeeeeeeee Meeee Meeeeeeee eeeeeee eee Meeeeeeeeeeeee Meee Meeee ee Meeee-8-eee eee Meeeeeeeeeee[888]
| Meeeee Meeeeeeeeeeee | ee | Meeee (%) | Mee |
|---|---|---|---|
| 888 | 88.8:8 | 88 | [888] |
| 888 | 8.8:8 | 88 | [888] |
| 888 | 8:8.88 | 88 | [888] |
| 888 | 8.88:8 | 88 | [888] |
M eeeeeee ee eeeeeeeeeeeeee eeeeeeee 888, eeeeeeeee eeee eeee eeeee-8-eee, eeee eeeee eeee eeeeeeeeeeee ee eee eeeeeeee ee 8 eee% ee eee eeeeee eeeeeeeeeeeee 888 ee eee eeeeeeeeeee ee eeeeee eee “eeeeeee” eeeee eeeeeee. Meeee eee eeeeee eee eeee eee eee eeeeeeeee eeeee eeeeeee eeee eeeeeeeeeeeeeeeeee, eee M-eeeeeeeeeee 888 eeeee eeeeeee (Meeeee 888).[888]
Meeeee 888 Meeee Meeeeeeee eeeeeee eee Meeeeeeeeeeeee Meeeeeee ee Meeeee Meeeeee eee Meeeeeeeeeee[888]
| M8 | ee | Meeee (%) | Mee |
|---|---|---|---|
| Me | 88.8:8 | 88 | [888] |
| Me | 88:8 | 88 | [888] |
| eMe | 88.8:8 | 88 | [888] |
| eMe | 8.88:8 | 88 | [888] |
| e-Me | 8.88:8 | 88 | [888] |
| Me | 8.88:8 | 88 | [888] |
| MMMMMM | 88.8:8 | 88 | [888] |
Me eeeeeeee, eee eeeeeeeeeeeeee eeee eeeee 888 ee eeeeeeeeeeeee eeeeee eeee eeeeeee eee-eeeeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeee ee eee eeeeee eeeeeeeeeeeee 888 ee eeee eee eeeee eeeeeee 888 ee eeee eeeeeeeeeeee eeeeee eee eeee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeee (Meeeee 888).[888] Meeeeeeeeeeee, eeeeeeeee eeee eeeeeeeeee eeeeeeeee ee eee eeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeee eeeeeeee.
Meeeee 888 Meeeeeeeeeeee-Meeeeeeee Meeee Meeeeeeee eeeeeee eee Meeeeeeeeeeeee Meee Meeee ee Meeeeeeeeeeee eee Mee-Meeeeeeeee Meeeeeeee[888]
| M8 | Meeee (eee/eeee) | ee ee eeee-888 | Meeee (%) | Mee |
|---|---|---|---|---|
| Me | 8:88 | 88.8:8 | 88 | [888] |
| MM=MMMe | >8:88 | 88.8:8 | 88 | [888] |
| M≡MMe | 8.8.8 | 88.8:8 | 88 | [888] |
| 8-eeeeeeee | >8:88 | 88.8:8 | 88 | [888] |
| MMe=MMMe | >8:88 | 88.8:8 | 88 | [888] |
Meeee ee e eeeeeeeeeee eeeeeee eee eeeeeeee ee eee eeeeeeee eeee eeeee eee eee eeeeeeeeeeeeeeeeee eeeeeeee ee eee eeeee eeeeee. Mee eeeeeee, ee eeeeeee eeeeeeee ee eeee eeeeeeeee ee eeeee eeeeeeee ee eeeee eeeeeeeee, eee (M)-eeeeeeeeeeeeee eeeeeee 888M ee eeeeee-8-eee eeeee eee eee-eeeeeeeeee eeeee eeeeeee 888M eeeeeeeeeee, eeeeeee eee M-eeeeee 888M eeeeeeee eee eeee-eeeeeeeeee eeeee eeeeeee 888M (Meeeee 888).[888]
Meeeee 888 Meeee Meeeeeeee ee (M)- ee (M)-Meeeeeeeeeeeee Meee Meeeee ee Meeeee-8-eee[888]
| Meeee Meeeeee | M8 | Meeee (eee/eeee) | ee | Meeee (%) | Mee |
|---|---|---|---|---|---|
| 888M | Me | 88:8 | 88:8 (eee) | 88 | [888] |
| 888M | 8-eeeee | 8:8 | 8:8 (eee) | 88 | [888] |
| 888M | (M)-MM=MMMe | 8:8 | 8:8 (eee) | 88 | [888] |
| 888M | Me | 8:8 | 8:8 (eee) | 88 | [888] |
| 888M | Me | 8:8 | 8:8 (eeee) | 88 | [888] |
| 888M | eeeee | 8:8 | 8:8 (eeee) | 88 | [888] |
Meeee eeeeeeeeeeeeeee eee ee eeeeeeee ee eeeeeeeeeeeeeeee eeeee-eeeee eeeeeeeee eeee ee eeeee eeeeeee eee eeeeeeee eeeeeeeeeeeeee eeee eeeeee 888M eee 888M eee eeeeeeeeeeee, eeeee eeeeee eee eeeeeeee eeeeeee 888M eee 888M, eeeeeeeeeeee. Meee, eee eeeeee eeeeeeeeeeeee 888 ee eeee ee eeeeee eeeeeeeee, eee eee eeeeeeeee eeeeee eeeeeeeee eee eeee eeeeeeee eeeeeeeee eeee eee eeee eeeeee eeeeeee eeeeeee ee eeeeeeeee eeee eeeeeeee eee eeeeeeee eeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeeeeeeeee ee eee Meeee Meeeeeeee eeeeeee eee (M)- eee (M)-Meeeeeeeeeeeee Meee Meeeee ee Meeeeeee eee Meeeeeeeeeee[888]
Meee eeeee eeeee eeeeeeeee eeeeeee eee eeeeeeeeeeeee eeee eeeee ee eeeeeeee eee eeeeeeeeee eeeeeeeee eee ee eeeeeee eee, eeeeeeee eeeeee eeeeeeeee eee eeeeee eeeeeeee eeeee eeee eeeeee eee eeeeeeee ee eeeee ee eeeeee eeee eeeeee ee eee eeeeeeee. Meeeeeeee eeeeeeeeeeeeeeeeeeee ee eeeeeeee eee eeeeeeee ee eeee eeeeeeeeeeeeeeeeee ee eeeeeeee.[888,888] Meee eeeee, eee eeeeeeeeeeee eeeeeeeee eee eeeeeeee ee eeeee eeeeeeee eeeeeee, eee eee eee-eeeeeeeeee eeeeeeee 888 eee eeeeeeeee eeee eee M-eeeeeeeeee eeeeeeeeeeeeee eeee eeeee 888M ee eee eeeeeeeee eee eee eeeeee eeeeeeeeeeeee 888 ee eeee ee eeeeeee eee eeeeeeeee (Meeeee 888).[888]
Meeeee 888 eee-Meeeeeeee Meeee Meeee Meeeeeeee eeeeeee Meeeeeeee eee eee M-Meeeeeeeee Meeeeeeeeeeeee Meee Meeee ee Meeeeeee[888]
| M8 | Meee (°M) | Meee (e) | Meeee (eee/eeee) | ee ee eee-888 |
Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| Me | −88 | 8 | 88:8 | 8.8:8 | 88 | [888] |
| (M)-MM=MMMe | −88 | 8 | 88:8 | 8.8:8 | 88 | [888] |
| (M)-MMe=MMMe | −88 | 8 | 88:8 | 8.8:8 | 88 | [888] |
| M≡MMe | −88 | 8 | 88:8 | 8.8:8 | 88 | [888] |
| (MM8)8Me | −88 | 88 | 88:8 | 8.8:8 | 88 | [888] |
| Me | −88 | 88 | 88:8 | 8.8:8 | 88 | [888] |
Me eeeeeeee, eeee eeee eeeeeeeeeeeeeeeeeeeeee eee eeeeeeee eeee eee M-eeeeeeeeee eeeeeeeeeeeeee eeee eeeee 888M ee eeeeeee eeee eee eeee eeeeeeeee eeeee eee eeee eeeeeeeeee (Meeeee 888).[888]
Meeeee 888 eeee-Meeeeeeee Meeee Meeee Meeeeeeee eeeeeee Meeeeeeee eee eee M-Meeeeeeeee Meeeeeeeeeeeee Meee Meeee ee Meeeeeee[888]
| M8 | Meee (°M) | Meee (e) | Meeee (eeee/eee) | ee ee eeee-888 |
Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| Me | −88 | 8 | 88:8 | 8.8:8 | 88 | [888] |
| (M)-MM=MMMe | −88 | 8 | 88:8 | 8.8:8 | 88 | [888] |
| (M)-MMe=MMMe | −88 | 8 | 88:8 | 88:8 | 88 | [888] |
| M≡MMe | −88 | 8 | 88:8 | 8.8:8 | 88 | [888] |
| (MM8)8Me | −88 | 88 | 88:8 | 8.8:8 | 88 | [888] |
| Me | −88 | 88 | 88:8 | 8.8:8 | 88 | [888] |
Me eeeeeeee, eeeeeeeeeeeeeeee eeeeeeeee eeeeeee eee eeeeeeeeeeeeee eeee eeeee 888 ee eeeeee eeeeeee eee eeeeeee ee eeeeeeee eeeeeeee eeeeeeee 888 eee ee eeeeeeee ee eee eee ee eee eeeeee eeeeeeee M-eeeee 888. Me eeee eeeeeeeee eee eeeeee ee eeeeeeeeeeeeeeeeee eeeeeee eeeeeee ee eee eeeeee eeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeeeeeeeeee Meeee Meeeeeeee eeeeeee eee Meeeeeeeeeeeee Meee Meeee ee Meeeee Meeeeee eee Meeeeee[888]
| M8 | M8 | ee | Meeee (%) | Mee |
|---|---|---|---|---|
| Me | Me | 88:8 | 88 | [888] |
| Me | M≡MM | 88:8 | 88 | [888] |
| 8-eeeeeeee | Me | 8.8:8 | 88 | [888] |
| 8-eeeee | Me | 8.8:8 | 88 | [888] |
| (MM8)8Me | Me | 8.8:8 | 88 | [888] |
| Me | Me | 8.8:8 | 88 | [888] |
| e-Me | Me | 8.8 | 88 | [888] |
Me “ee eeee” eeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeee eeeee eeeeeee eeeeeeeeeeeee eeee eeeeee 888 ee eeeee eeeeeeeee eeee eeeeeeeee eeeeeee ee eeeeeee eeeeeeeeeeeee eee e eeeeeeeee eeeeee ee eee eeeeee eeeeeeeeeeeee 888.[888,888] Me eeee eee eee eeeee eeeeeee 888 eee ee eeeeeeee ee eeeeee eeeeeeeeeeee eeeeee eee eeee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeee (Meeeee 888).[888] Me ee eeeee eeeeee eeee eeee eeeeee eeeeeee eee eeee, eeeee eeeeeeee eee ee eeeeeeeee eeee eee eeeeeeeeeeeeeeeeeeee ee eee eeeee eeeeeee eeeeeeee, eee eee eeee-eeeeeee eee eeeeeeee eeeeeeeee ee eeeee eeee.
Meeeee 888 Meeee Meee Meeeeeeee Meeee Meeeeeeee ee Meeee Meee Meeeee ee eee Meeeeeee ee Meeeeee Meeeeeeeeeeee[888]
| M8 | M8 | M8 | M8 | Meeeeeeeeee | Meeee (eeee/eee) | ee ee eeee-888 | Meeee (%) | Mee |
|---|---|---|---|---|---|---|---|---|
| MMMMM | M | MMe | Me | M | – | 88:8 | 88 | [888] |
| MMMMM | M | MMe | 8-eeeee | M | – | 88:8 | 88 | [888] |
| MMMMM | Me | MMe | Me | M | 88:8 | 8.8:8 | 88 | [888] |
| MMMMM | Me | Me-Me | Me | M | 88:8 | >88:8 | 88 | [888] |
| MMMMM | Me | MMe | (MM8)8Me | M | 88:8 | 88:8 | 88 | [888] |
| MMMMM | Me | MMe | Me | M | 8.8:8 | 8.8:8 | 88 | [888] |
| MMM | M | Me | Me | M | – | >88:8 | 88 | [888] |
| MMM | M | Me | 8-eeeee | M | – | 88:8 | 88 | [888] |
e M: (M,M)-888 (8 eee%), MeMe8 (888 eee%), MM8Me8, −88°M; M: (M,M)-888 (8 eee%), MeMe8 (888 eee%), MM8Me8, −88°M; M: (M,M)-888 (8 eee%), MeMe8 (888 eee%), MMMM (88 eee%), MM8Me8, −88°M, 88 e; M: (M,M)-888 (88 eee%), MeMe8 (888 eee%), MMMM (88 eee%), MM8Me8, −88°M, 88 e; M: (M,M)-888 (8 eee%), MeMe8 (888 eee%), eMe8MMe, MM8Me8, −88°M, 8–88 e.
Meeeeeee eee eeee-eeeeeeeeeeeeeeeeee eeee eeeeee ee eeeeeee,[888] eeeeeeeeee eeeeee,[888] eeeeee,[888] eee eeeeeeeeee eeeeee[888] eee eeeee eeee e eeeeeee ee eeeeeeeee eeeee eeeee eeeeeeeeee, eeeeeeeeee eeeeeeee eeeeee eeeeeee ee eee eeeee eeee eeeeee ee eeeeeeeeee eeeeeeee eeeeeee eeee ee eeeeeee eeee eeeeeeeeee eeeeeeeee. Meeeeee, eeee eeeeeeeeee eeeeeeeee eeeee eeeeee eeeeeee (e.e., 888, M8 = MMMMM; M8 = Me; M8 = MMe) ee eeee eeeee eeeeeee eeee eeeeeeeeee eeeeeeeee eee eeeee eeeeeee eee ee eeeeeeee ee eeeeeeee eeeeee; eeeeeeee, eeee eee eeeeee eeee eeee eeeeeeeee- eee eeeeeeeeeeeeeeeeee.
Meeeeeeeeeeeee eeee eeeeee ee eeeeee α-eeeeeeeeee eeeeeee eee ee eeeeeeee ee eeeeeee Meeee eeee eeeeeeeee eeeee eeeeeeeee eeeee eeeeeeeeeeeeee, eee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeee eeee eeee eeeeee eeeeeeeee-eeeeeee eeeeeeeeeeeee. Meee eeee eeee eeeeee eeeeeeeeeeeeee ee “eeeeeee” eeeee eeeeeeeee ee eeeeeee eeeeeee/eeeeeeeeee eeeeeeeee eee eeeee[888] eee, eeeeeeeee eeee eee eeeeeeeee ee eee eeeeeeee, eeee eeeeeeeeeeeeeeeeeeee eee eeeee. Meeeeeee, eee eeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee eeee eeeeeee eeee eee eeeeee ee eee α-eeeeeeeeeee ee eee eeeeeeeee.[888] Mee eeeeeee, eeeee eee M,M-eeeeeeeeee ee eee eeeeee eeeeeeeeeeeee 888 eee eeeeee α-eeeeeeeeee eeeeeee 888 eeeee eeee eeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eee-eeeee eeeeeee 888M ee eeeeeeeeee ee eee eeee-eeeeeeeeeeeee 888M; eeeeeee, eeee eee M,M-eeeeeeeeee eeee eeeeeeeeeeeeee ee eeee eeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeee eee Meeeeeeeee Meeee ee Meeee Meeeeeeee Meeeeeeee Meeeee Meeeeeeeeeeeee Meee Meeeee[888]
| M8 | Meeeee ee 888 | Meeee (eee/eeee) | Meeee (%) | Mee |
|---|---|---|---|---|
| MMMMM | M,M | 88:8 | 88 | [888] |
| MMMMM | M,M | 8.8:8 | 88 | [888] |
| MMe-Me | M,M | 88:8 | 88 | [888] |
| MMe-Me | M,M | 8.8:8 | 88 | [888] |
| Me | M,M | 88:8 | 88 | [888] |
| Me | M,M | 8:8.8 | 88 | [888] |
Mee eeeeeee ee eeeeeee eeee ee eee “eeeeeeeeee” eeeee eeeeee eeee eeee eeee eeeeeeee,[888–888] eee eeee eee eeeeee eeeeeeeeeeeeee eeee eeeee 888 ee eeeee ee eeeee eeeeeeeeeeeeee eeee eee eeeeeeeeeee ee eee eeeeee eeeeeeeeeeeee 888 eee ee eeeeee eee eeeeeeeeeeeee eeeeeeeeeeeee 888 eeee eeee eeeeeee ee eeeeeeee eeeeeeeeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeee eee Meeeeee Meeeeeeeeeeeeee ee eee “Meeeeeeeee” Meeee Meeeee[888]
| M8 | Meeeee ee 888 | eee/eeee (eeeeeeee) | eee/eeee (eeeeeeee) | Meeee (%) | Mee |
|---|---|---|---|---|---|
| Me | M,M | 8:88 | 88:8 | 88 | [888] |
| Me | M,M | 88:8 | 88:8 | 88 | [888] |
| (M)-MM=MMMe | M,M | 8:8 | 88:8 | 88 | [888] |
| (M)-MM=MMMe | M,M | 8:8 | 88:8 | 88 | [888] |
| (M)-MM=MMMe | M,M | 8:8.8 | >88:8 | 88 | [888] |
| (M)-MM=MMMe | M,M | 8.8:8 | >88:8 | 88 | [888] |
Meeee Meeee eeee eeeeeeeee eeeee eeeeeeeee ee eeeee eeee eeeeee eeee eeee eeee eeeeeeeee,[888–888] eee eee eeeeee eeeeee 888, eee eeeeeee, eeeeee eeee eeeeeeeee eeeee eeeeeee 8-eeeeeeeeeeeee-8-eee (888) ee e eeeeeeee ee eeee eee eeeee eeeeeee 888 (Meeeee 888).[888] Meeeeee eeeeeeeeeeeee eee eeee ee eeee ee e eeeeeeee, eee ee eeeeeee eeee eeeeeeeeee eeeeeeee eeeee eee eeeeeeeee eeeeeeee.[888]
Meeeee 888 Meeeeeeeee ee Meeeeeeee Meeeeeeeeeee ee Meeee Meeeeeeee[888]
| M8 | Meeeeee | Meee (°M) | Meee (e) | Meeee (%) | Mee |
|---|---|---|---|---|---|
| 8-Mee | MMM | −88 | 8.8 | 88 | [888] |
| 8-MeMM8M8 | eeeeeeee | 8 | 8 | 88 | [888] |
| 8-MMM8M8 | eeeeeeee | 8 | 8 | 88 | [888] |
| 8-MeM8M8 | MMM | −88 | 8 | 88 | [888] |
| 8-MeM8M8 | MMM | −88 | 8 | 88 | [888] |
| (MM8)8Me | MMM | −88 | 8 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
(M)-8-Meeeeee-8-eeeeeeeeeeee-8-eee (888, M8 = Me):[888]
Mee eeeeeeeeeeeeee eeeeeee 888 (M8 = Me; 888 ee, 8.8 eeee, 8.8 eeeee) eee eeeee eeeeeee ee e eeee ee (M,M)-888 (88.8 ee, 8.8 eeee, 8.88 eeeee) ee MM8Me8 (8 eM) eeee ee −88°M. MeMMM (888 µM, 8.8 eeee) ee MM8Me8 (8 eM) eee eeeeee ee −88°M eee eeeee eeeeeee eee e eeeee eeeeeee ee eee eeeee eeee. Meeeee eee eeeeeeee eee eeeeeeeeeee ee eee eeeeeee eeee ee −88°M, eee eeee eeee eee eeeeeeeeee eee eee eeeeeee eee eeee eeeeeee ee −88°M eee 8 e, eeeeee ee eee eeeeeee eeeeee eeee eee. ee MeMMM8 eeeeeeeeee eeeeee ee 8°M. Mee eeeeee eee eeeeeee eee 88 eee, eee eeee eee eee-eeeee eeeeeee eee eeeeeeee eeeeeee Meeeee. Mee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeee eeeee eee eee eeeeeeee eeee eeeeeeee, eeeee (Me8MM8), eee eeeeeeee, eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/Me8M 8:8) ee eeee e eeeee, eeeeeeeee eee; eeeee: 888 ee (88%).
(8M,8M)-8-(Meeeeeeeeeeeeee)-8-eeeeeeeeeeee-8-ee (888M):[888]
Mee (M)-eeeeeeeeeeeeee eeeeeee 888M (888 ee, 8.8 eeee, 8.8 eeeee) eee eeeee ee e eeee ee eee eeeeeeeeeeeeeeee (M,M)-888 (88 ee, 8.8 eeee, 8.88 eeeee) ee MMMe8/MM8Me8 (8:8; 8 eM) eeeeeeeeee ee −88°M, eee eee eeeeeee eee eeeeeee eee 88 eee. Meeeeee eeeeeeeee MeMMM (8.888 eM, 8.8 eeee, 8.8 eeeee) eee eeee eeeee eee, eeeee 8 e ee −88°M, MeMM (88 eM) eee eeeeeeeeee. Mee eeeeeee eee eeeeeee ee −88°M eee 88 eee, eee eeee eeee eee eeeeeee, eee eee eeeeeee eee eeeeeee ee eeee ee ee (eeeee eeee 8.8 e), eeeeee ee eee eeeeee eeee eee. ee MeMMM8 eeeeeeeeee eeeeee ee 8°M, eee eee eeeeeee eee eeeeeee eee 8 e. Mee eeeeeee eee eeeeeeee eeeeeee Meeeee, eee eeee eee eeeeeeee eee eeeeee eeee eeeeeee/Me8M (8:8; 88 eM). Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee eeee eeeeeee/Me8M (8:8; 88 eM). Mee eeeeeee eeeee eee eee eeeeeee eeee eeeeeeee, eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8), eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee ee eeee eee eeeee eeeeeeee ee e eeeee, eeeeeeeee, eeeee eeeeee; eeeee: 888 ee (88%).
eeee-Meeee (8M,8M)-8-Meeeeee-8-eeeeee-8-eeeeeeeeeeeeeeee (888, M8 = Me; M8 = Me-Me; M8 = Me):[888]
MMMMMMM: Meeeeee eeeeeeeeeeeee eeeee eeeeeeee eeeeeeeee eee eeee eee eeeeeeeeeee eeeeee. Mee eeeeee eeeee eee eeee eee eeee.
MeMMM (888 µM, 8.8 eeee, 8.8 eeeee) eee eeeee ee e eeeee-eeeee, eee-eeeeee 88-eM eeeee eeeeeeeeee e eeee ee eee eeeeeeeeeeeeeeee (M,M)-888 (8.8 ee, 8.88 eeee, 8.88 eeeee) ee MM8Me8 (8 eM), eeeeeeeeee eeeeee ee −88°M eee eeeeeeeee eeeee M8. MeMe8 (888 µM, 8.8 eeee, 8.8 eeeee) eee eeee eeeee, eee eee eeeeeee eee eeeeeee ee eeee ee −88°M eee 8 eee. Mee eeeee eeee eeeee 888 (M8 = MMMMM; M8 = Me; M8 = Me-Me; 888 ee, 8.8 eeee, 8.8 eeeee) eee eeeee eeeeeeee (eeee 8 eee) eee eee eeeeeeeee eeeeeee eee eeeeeee ee −88°M (eeee eeeeeeeeeee) eee 8 e, eeeeee ee eee eeeeee eeee eeeee eeeeeeee eeee 8:8 eeeeeee ee eee. ee MM eee 8.8 M MM8MM8 eeee (88 eM). Meee eeeeeeee eeeeeee eee eeeeeee eeeeeeeeee eee 8 e, eee eeee eeeeeeee eeeeeee Meeeee. Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeee eee eeeeeeee eeee eeeeee eeee eeeee (88 eM), eeeee [Me8MM8 (8 e)], eee eeee eeeeeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee ee eeeeee e eeeeeeeee eee; eeeee: 888 ee (88%).
8,8-Meeeeeee-8-(eeeeeeeeeeeeeee)eeeeeeeeeee 888: Meeeeee Meeeeeeee:[888]
8.88 M MeMe ee Me8M (8.88 eM, 8.88 eeee) eee eeeee ee e eeee ee eeeeeeeeee-8-eee (88.8 ee, 8.88 eeee) ee MMM ee 8°M. Mee eeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee, eee MMM (8.8 eM) eee eeeee ee eee eeeeeee ee eeeeee e eeee ee eeeeeee 8-eeeeeeeeeeeee-8-eee ee MMM.
Mee eeeee eeeeee eeeeee 888 (8.88 eeee) ee MMM (8.8 eM), eeeeeeee ee e eeee ee ee eeeeeeee (8.88 eeee) ee MMM (8.8 eM), eeee eeeee ee 8.8 M eeeeeee 8-eeeeeeeeeeeee-8-eee ee MMM (8.8 eM, 8.88 eeee) ee −88°M, eee eee eeeeeee eee eeeeeee ee −88°M eee 8 e. Mee eeeeeeee eee eeeeeeee ee eeeeee eee. ee MM8Me, eee eee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeee MMM (eeeeee eee, eeeeee/MeMMe 8:8) ee eeee eee eeeeeeeee eeeee eeeeee.
References
| [320] | Meeeeee, M. M.; Meee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [538] | Meeeeee, M. M.; Meeeee, M. M. M.; Me, M.; Meee, M.-M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [539] | Meeeeee, M. M.; Meeeeeeee, M. M., Mee. Meee. Mee., (8888) 88, 888. |
| [540] | Meeeeee, M. M.; Mee, M., Meee. Meee. Meee. Mee. M. M. M., (8888) 888, 8888. |
| [541] | Meeeeee, M. M.; Meeeeeee, M., Me Meeeee Meeee Meeeeeeee, Meeeeeee, M., Me.; Meeee-MMM: Meeeeeee, Meeeeee, (8888); Mee. 8, e 888. |
| [542] | Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M. M.; Meee, M.-M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [543] | Meeeeee, M. M.; Meeee, M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [544] | Meeeeee, M. M.; Meeeeeeee, M. M.; Meee, M.-M.; Me, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [545] | Meeeeee, M. M.; Meeeeeeee, M. M.; Meee, M.-M., M. Mee. Meee., (8888) 88, 888. |
| [546] | Meeeeee, M. M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [547] | Meeeeee, M. M.; Meeeeeeee, M. M.; Meee, M.-M., Meeeeeeeeee, (8888) 88, 88888. |
| [548] | Meeeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [549] | Meeeeee, M. M.; Mee, M., M. Mee. Meee., (8888) 88, 88888. |
| [550] | Meeeeee, M. M.; Mee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [551] | Meeeeee, M. M.; Meeeeeee, M. M., Me., Mee. Meee., (8888) 8, 8888. |
| [552] | Meeeeee, M. M.; Meeeeeee, M. M., Me., M. Me. Meee. Mee., (8888) 888, 8888. |
| [553] | Meeeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [554] | Meeeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [555] | Meeeeee, M. M.; Meeeeeee, M., Meeeeee, (8888), 8888. |
| [556] | Meeeeee, M. M.; Meeeeeee, M., Mee. Meee., (8888) 8, 8888. |
| [557] | Meeeeee, M. M.; Meee, M. M., Mee. Meee., (8888) 8, 8888. |
| [558] | Meeeeee, M. M.; Meeeeeee, M., Mee. Meee., (8888) 8, 8888. |
| [559] | Meeeeee, M. M.; Meeeeeee, M.; Meee, M. M., M. Mee. Meee., (8888) 88, 88888. |
| [560] | Meeeeeee, M.; Meeeeeeee, M., Meee. Meee., (8888), 888. |
| [561] | Meeeeeee, M.; Meeeeeeee, M., Meee. Meee., (8888), 888. |
| [562] | Meeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meee. Meee. Meee, (8888) 88, 8888. |
| [563] | Meeeeeee, M.; Meeeeee, M. M.; Meeeee, M.; Meeeeee, M.; Meeeeeee, M. M.; Meeeee, M., Meee. Meee., (8888), 888. |
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