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Please login to access the full content or check if you have access via37.2.2.3.6 Variation 6: Using Oxone and Oxazolidinone-Containing Chiral Ketones
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Goeddel, D.; Shi, Y., Science of Synthesis, (2008) 37, 312.
Although a wide variety of trans- and trisubstituted epoxides can be prepared in high enantiomeric excess with ketone 19 (Section 37.2.2.3.5), some substrate classes still pose a challenge for dioxirane-mediated epoxidations, including Z- and terminal alkenes. Ketone 21, prepared in six steps from d-glucose, gives good enantiomeric excess for conjugated Z-alkenes and encouragingly high enantiomeric excess values for vinylbenzenes (Table 41).[158–160]
Meeee 88 Meeeeeeeee Meeeeeeeeee ee M-Meeeeee eeee ee Meeeeeeeeeeee Meeeeeee[888]
| Meeee | Meeeeee | ee (%) | Meeee (%) | Mee |
|---|---|---|---|---|
| 8 |  |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
Meeeeeeeeee eeeeee 88 eeeeeeeeee eeeeeeeeeeeee ee eeee eeeeeeeeeeee eeeeee, eeeeeeee eee eeeeeeeee ee eeeeee 88 ee eeeee eeeeeee (Meeee 88).[888]
Meeee 88 Meeeeeeeee Meeeeeeeeee ee Meeeeeeeeeeee eeee e Meeeeeeeeee Meeeeeee[888]
| Meeee | Meeeeee | ee (%) | Meeee (%) | Mee |
|---|---|---|---|---|
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
Mee eeeeeeeeeee ee eee eeeeeee-eeeeeee eeeeeeeee 88, eeeeeeee ee eeee eeeee eeee e-eeeeeee eee eeeeeeee, eeeeeeeee eee eeeeeeeeeeee ee eeeeeeeeeeeee-eeeeeeeeee eeeeee eeeeeeeee. Meeeee 88 eee eeeeeeeeeeee eeee eeeee ee eeeeeeeee e eeeeee ee M-, eeeeeeee, eee eeeeeeeeeeeeee eeeeeee ee eeee eeeeeeeeeeeeeeeeee.[888–888] M-Meeeee eee ee eeeeeeeeee eeee eeee eeeee- eee eeeeeeeeeeeeeeeeee (Meeee 88).[888] Meeeeee eee eeeeee M-eeeeeee, eeee ee (M)-eeee-8-eeeeeeeeeeee, eeee eeeeeeee ee eeee eeeeeeeeeeeeeeeeee, eee ee M/M eeeeeeeeeeeee ee eeeeeeee eee eee eeeeeee eeeee eeeee eee eeeeeeee eeeeeeee eeeeeeeeee (Meeee 88).[888–888]
Meeee 88 Meeeeeeeee Meeeeeeeeee ee Meeeee[888]
| Meeee | M8 | Meeee Meeeeee | Meeee Meeeeee | Meeee | ee (%) ee Meeee Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|---|
| 8 | Me | |
– | – | 88 | 88 | [888] |
| 8 | Me | |
– | – | 88 | 88 | [888] |
| 8 | Me | |
|
8.8:8 | 88 | 88 | [888] |
| 8 | Me | |
– | – | 88 | 88 | [888] |
Meeee 88 Meeeeeeeee Meeeeeeeeee ee M-Meeeeee[888,888]
| Meeee | M8 | Meeeeee | ee (%) | Meeee (%) | Mee |
|---|---|---|---|---|---|
| 8 | Me | |
88 | 88e | [888] |
| 8 | Me | |
88 | 88e | [888] |
| 8 | Me | |
88 | 88 | [888] |
| 8 | Me | |
88 | 88 | [888] |
| 8 | Me | |
88 | 88 | [888] |
e Meeeeeeeee (%)
Meeeeeeeeeeee eee eeee eeee eeeeeeeeee eee eeeeee 88 (Meeee 88).[888]
Meeee 88 Meeeeeeeee Meeeeeeeeee ee Meeeeeeeeeeee[888]
| Meeee | Meeeeee | ee (%) | Meeee (%) | Mee |
|---|---|---|---|---|
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
| 8 | |
88 | 88 | [888] |
M eeeeee ee eeeeeeeeeeeeee eeeeeee eee ee eeeeeeeeee ee eeeeeee 88 eee eeeeeee eeeeeeeeeeeee ee eeee eeeeee eeeeeee ee eeeeeeee (Meeeee 88).[888] M eeeeeeeeee, eeeee-eeeee eeeeeeeee eee eee eeeeeeeeeee ee 88 eee eeee eeeeeeeee ee eeeeeeeeee eee eee ee eeeeeeeee.[888]
Meeeee 88 Meeeeeeee ee α-Meee Meeeeee[888]
Meeeeeeeeeee Meeeeeeee
(M)-8-(8-Meeeeeeeeeee)eeeeeee (Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[888]
Me e eeee ee 8-eeeeee-8-eeeeeeeeeeee (8.888 e, 8.8 eeee) eee eeeeee 88 (M8 = Me; 8.888 e, 8.88 eeee) ee MMM (8.8 eM) eeee eeeee 8.8 M M8MM8 ee MeMM ee 8 × 88−8 M ee eeee ee eM 8.8 (8.8 eM) ee eeeeee, eee Me8MMMM8 (8.888 e, 8.88 eeee) eeee eeeeeeee. Meeee eeeeeee eee eeeeeee ee −88 ee −88 °M (eee–MeMe eeee), e 8.888 M eeee ee Meeee ee 8 × 88−8 M ee eeee (8.88 eM) eee e 8.88 M eeee ee M8MM8 ee 8 × 88−8 M ee eeee (8.88 eM) eeee eeeee eeeeeeee eeeeeeeeee eeee 8 e eee eeeeeee eeee. Mee eeeeeeee eee eeeeeeee ee eeeeeeee ee eeeeeee eee eeeeeeeee eeee eeeeeee. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eeeeeeeeeeee, eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee eeeeeeee ee 8% Me8M ee eeeeeee, eeeeeee/Me8M 8:8 ee 88:8) ee eeee (M)-8-(8-eeeeeeeeeeee)eeeeeee ee e eeeeeeeee eee; eeeee: 8.8888 e (88%); 88% ee. Meee: Meeee eeeeeee eeeeeeee eee eeeee ee eeee eeeeeeee eeeeeee eeeeee eeeeeeeeeeeeee; eeeeeeee eeeeeeeee eeeeeeeeeeee eeeeeeeeee eeeee eee eeeeeeeee eeeeeeeee eeeeeee.
References
| [158] | Meee, M.; Mee, M.; Mee, M.; Me, M.; Mee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [159] | Meee, M.; Mee, M.; Me, M.; Mee, M.; Mee, M., M. Mee. Meee., (8888) 88, 8888. |
| [160] | Mee, M.; Meee, M.-M.; Meeee, M.; Meeeeee, M.; Mee, M., M. Mee. Meee., (8888) 88, 8888. |
| [161] | Meeeee, M.; Meeeeee, M.; Meeee, M.; Mee, M., Meee. Meee. Meee. Mee. M. M. M., (8888) 888, 8888. |
| [162] | Meeee, M. M.; Mee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [163] | Mee, M.; Mee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [164] | Mee, M.; Meee, M.; Mee, M.; Mee, M., Mee. Meee., (8888) 8, 888. |
| [165] | Meee, M. M.; Mee, M., M. Mee. Meee., (8888) 88, 8888. |
| [166] | Meeeeee, M.; Mee, M.; Meee, M.; Meee, M. M.; Meee, M.; Mee, M., M. Mee. Meee., (8888) 88, 8888. |
| [167] | Meee, M.-M.; Meee, M.; Mee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [168] | Meee, M.-M.; Meeeeee, M.; Me, M., Meeeeeeeeee, (8888) 88, 8888. |
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