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Please login to access the full content or check if you have access via41.1.1.5.54 Method 54: Addition to a Nitroalkene Using a Carbanion Prepared from a 1,3-Diester
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Aitken, R. A.; Aitken, K. M., Science of Synthesis, (2010) 41, 184.
In Scheme 201 (Section 41.1.1.5.19) is shown a reaction of a malonate with a nitroalkene in a tandem cyclization reaction. Deprotonated malonate esters have been useful reagents in many kinds of nucleophilic reactions, and have also been used extensively in Michael additions to nitroalkenes. Examples are shown in Schemes 257 and 258.
Meeeee 888 Meeeeeee ee Meeeeeee Meeeee ee Meeeeeeeeeee[888,888,888–888]
M8 | M8 | M8 | M8 | M8 | Meeeeeeeeee Meeeee (M/M)e | Meeeeeeeee | Meeeee (%) | Mee | Meeeeeeeeeeee ee Meeeeeee | Meeeeeee Meeeeeee |
---|---|---|---|---|---|---|---|---|---|
Me | M | 8-MeMM8M8 | M | M | e.e. | eee eeeeeeee eeeeee ee eeee MeMMe/MeMM | eeee eeeeeeee ee eeeeeeeeeee (eeeeeeeeee), eeee ee MeMM, M8M | 88 | [888] |
Me | M | Me | M | Me | e.e. | eee eeeeeeee eeeeee ee eeee eeeeeeeeee ee Me ee eeee eeeeeee | eeee eeeeeeee ee eeeeeeeeeee, eeee MeMM, M8M | e.e. | [888] |
Me | Me | M | M | M | – | eeee MeMMe/MeMM, eeeeeee-8,8,8-eeeee | eeeeeeee ee eeeeeeeeeee eeee 8 e, −88°M ee ee, 8 e, eeee MeMM, M8M | 88 | [888] |
Me | M | M≡MMe | M | M | e.e. | eeeeeeee ee eeeeeeee ee MeMMe/MeMM, ee | eeeeeeee ee eeeeeeeeeee eeee 88 eee, −88°M, 8 e, eeee ee, eeee ee MMe | e.e. | [888] |
Me | M | Me | Me | M | e.e. | MeMMe, MeMM | eeeeeeee eeeeeeee ee eeeeeeeeeee, 88°M ee ee, 8 e, eeee ee MeMM | 88 | [888] |
Me | M | M | M | e.e. | Me, MeMM | eeee eeeeeeee ee eeeeeeee eeeee eeeeeeeeeeeee, eeee, 8.8 e, eeee MeMM, eee | 88e | [888] | |
Me | M | Me | Me | M | M | MeM, MMM, 8°M, 88 eee | MMM, 8°M, 88 eee, eeee ee MeMM | 88 | [888] |
Me | Me | Me | Me | M | M | MeM, MMM, 8°M, 88 eee | MMM, 8°M, 88 eee, eeee ee MeMM | 88 | [888] |
Me | MM8MM=MMe8 | Me | M | M | M | MeM, MMM, 8°M, 88 eee | −88°M, 8 e, eeee eM 8 eeeeeeeee eeeeee | 88 | [888] |
Me | M | (MM8)8MM8 | M | M | M | Me, MeMM, 88°M | eee eeeeeeeeeee eeee 8.8 e, <88°M, eeee ee, 8.8 e, eeee M8M, ee MMe | 88 | [888] |
Me | M | MM8 | M | M | M | MeM, MMM, ee, 8 e | eeeeeeee eeeeeeee ee eeeeeeeeeee, eeee ee, 88 e, eeee ee MM8Me | 88 | [888] |
e e.e. = eee eeeeeeee.
e Meeee eeee eee eeeee; eeeeeee eee eeeeeeeeeee eeeeeeeeeeee.
Meeeee 888 Meeeeeeeeeeeeee ee Meeeeeee Meeeee[888,888]
Meee eeeeeeee, eeeee eeeeeeeee eee eeeeeeeeeeeeeee eeee eeee ee eeeeeeee ee eeeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeeee ee eeee eeeee eee ee ee eeeeeeeeeeeeeeee eeeeee. Meeeeeee eeeee eeeeeeeee 888–888 eee eeeee ee Meeeeee 888 eee 888.
Meeeee 888 Meeeeeeee Meeeeeeeeeeeeee Meeeeeee ee Meeeeeeee ee Meeeeeeeeeee[888–888]
M8 | M8 | M8 | Meeeeeee (eee%) | Meeeeeeeee | Meeee Meeeeeeeee | ee (%) | Meeee (%) | Mee |
---|---|---|---|---|---|---|---|---|
Me | M | Me | 888 (888) | MMM, 8°M ee ee, 8 e | 888M | 88 | 88 | [888] |
Me | M | Me | 888 (88) | MMM, −88°M, 88 e | 888M | 88 | 88 | [888] |
Me | M | Me | 888 (8) | eeeeeee, −88°M, 88 e | 888M | 88 | 88 | [888] |
Me | M | Me | 888 (8) | eeeeeee, −88°M, 88 e | 888M | 88 | 88 | [888] |
Me | M | Me | 888 (88) | MM8Me8, −88°M, 88 e | 888M | 88 | 88 | [888] |
Me | M | Me | 888 (88) | eeeeeee, 88°M, 88 e | 888M | 88 | 88 | [888] |
Me | M | 8-Mee | 888 (88) | eeeeeee, 88°M, 8 eee | – | – | 88 | [888] |
Me | M | Me | 888 (88) | e-eeeeee, ee, 88 e | 888M | 88 | 88 | [888] |
Me | Me | Me | 888 (88) | e-eeeeee, ee, 888 e | 888M | 88 | 88 | [888] |
Me | M | eeee | 888 (88) | MMMe8, ee | 888M | 88–88 | 88–88 | [888] |
Me | M | Me | 888 (88) | eeeeeee, −88°M | – | 88 | 88 | [888] |
Me | Me | Me | 888 (8.8), Me(MMe)8 (8), 8-eeeeeeeeeeeeeeee (8.8) | MMMe8, ee, 88 e | 888M | 88 | 88 | [888] |
Meeee e eeeeeeeee eeeeeee ee eeeeee 888 ee eeeeeeee, eeeeeee 8-eeeeeeeeeee eeeeeeeee (M8 = Me, Me; M8 = Me, M, Me, MM8MM=MM8, MMMee, MMMe, MMe) eeee eeee eeeee ee (M)-8-eeeee-8-eeeeeeeeeeee, eeeeee eee eeeeeeee eeeeeeee ee 88–88% eeeee eee 88–88% eeeeeeeeeeee eeeeee. Mee eeeeeeee ee eeeeeee 8-eeeeeeeeeeeeee ee eeeee ee Meeeee 888.[888]
Meeeee 888 Meeeeeeee Meeeeeee ee Meeeeee 8-Meeeeeeeeeeeee ee e Meeeeeeeeee[888]
Meeeeeeeeeeeeee eeeeeeee ee eeeeeeeee ee eeeeeeeeeeee eee eeee eeee eeeeeeee (Meeeee 888).[888,888]
Meeeee 888 Meeeeeeeeeeeeee Meeeeeee ee Meeeeee Meeeeeee ee e Meeeeeeeeee[888,888]
Meeeeeeeeeee Meeeeeeee
Meeeeeee 8-(8-Meeeeeeeee)eeeeeeee (888); Meeeeee Meeeeeeee:[888]
Me (8.88 e, 88 eeee) eee eeeeeeeee ee MeMM (888 eM) eee eee eeeeeee eee eeeeee, eeeee eeeeeeee eeeeeeee (888; 88 eM, 88.88 e, 888 eeee) eee eeeee. M eeeee eeeeee ee eeeeeee-8,8,8-eeeee eee eeeee eee eee eeeeeee eee eeeeee ee −88°M. Meeeeeeeeee eeee eeeeeeeeeee, eeeeeeeeeee (888; 8.8 eM, 8.88 e, 88 eeee) eee eeeee eeee eeeeeeee eeee 8 e. Mee eeeeeee eee eeeeeee ee −88°M eee 8 e eee eeee eeeeeee ee eeee ee ee eeee 8 e. Mee eeeeeee eee eeeeee ee −8°M eee eee MMe(e) eee eeeeee eeeeeee eeeee eee eeeeeee eee eeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeee ee ee eeeeeee eee eeeeeeee ee eeeeee eee eeeeeeeee MeMe. Mee eeeeeeee eee eeeeeeeee ee eeee 888; eeeee: 8.8 e (88%); ee 888°M/8.8 Meee.
Meeeeee 8-(8-Meeeee-8-eeeee-8-eeeeeeeee-8-ee)eeeeeeee (888); Meeeeee Meeeeeeee:[888]
Me e eeeeeeeeee ee MeM (88 ee, 8.8 eeee) ee MMM (8 eM) ee 8°M eee eeeee eeeeeee eeeeeeee (888; 888 ee, 8.888 eeee), eeeeeeee ee eeeeeeeeeee 888 (888 ee, 8 eeee). MMM eeeeeeee eeeeee eeee eee eeeeeeee eee eeeeeeee eeeeee eeeeeeeeeee. Mee eeeeeee eee eeeeee eeee 8% ee MeMM eee eeeeeeeee eeee MM8Me8 (8×88 eM). Mee eeeeeeee eeee eeeeee eeee M8M (88 eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee ee eeee 888; eeeee: 888 ee (88%); 8M MMM (MMMe8, δ): 8.88 (e, 8M, M = 88.8 Me), 8.88 (e, 8M, M = 88.8 Me), 8.88–8.88 (e, 8M), 8.88 (e, 8M), 8.88 (ee, 8M, M = 88.8, 8.8 Me), 8.88 (ee, 8M, M = 88.8, 8.8 Me), 8.88 (e, 8M), 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me 8.88 (e, 8M, M = 8.8 Me).
Meeeeee (M)-8-Meeeee-8-(8-eeeee-8-eeeeeeeeeee)eeeeeeee (888); Meeeeee Meeeeeeee:[888]
M eeeeeee ee Me(MMe)8 (88.88 ee, 8.888 eeee), eee eeeeee eeeeee 888 (88.88 ee, 8.888 eeee), eee MMMe8 (8.8 eM) eee eeeeeee eee 88 eee, eeeee eeeee M8M (8.8 μM) eee eeeee. Mee eeeeeeeee eeeeeee eee eeeeeee eee 8 e, eeeee eeeee MMMe8 (8.8 eM) eee eeeeeeee 8-Å eeeeeeeee eeeeee (888.8 ee) eeee eeeee ee eee eeeeeee, eee eeeeeeee eee eeeeeeeee eee e eeeeeee ee 8 e. Mee M8M eeeeeee eee eeee eeeeeeeeee ee Meee Meeeeee eeeeeeeee. Me eee M8M eeeeeee eee >88 eee, eeeeeeee eee eeeeeeeee eee eeeeeeeeee eeeeeeeee eeeeee eeee eeeee. Meee eee M8M eeeeeee eee <88 eee, M8(e) eee eeeeeee eeeeeee eee eeeeeee eee e eeeeeee ee 8 eee eee (M)-8-eeeee-8-eeeeeeeeeeee (8.88 e, 8.88 eeee) eee eeeee ee e eeeee eeee 8 eee. MMMe8 (8 eM) eee eeeee ee e eeeee, eeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeeeeeeeee (8.88 e, 88.88 eeee) eeee 8 eee eee eeeeeee. 8-Meeeeeeeeeeeeeee (88.8 μM, 88.8 ee, 8.888 eeee) eee eeeee eeeeeee eee eeeee, eeeee eeeee M8 eee eeeeeee eeeeeee eee eeeeeee eee e eeeeeee ee 8 eee. Mee eeeeeee eee eeeeeee eeeee M8 ee ee eee 88 e. Meeee eeee eeee, MMMM eeeeeeee eeeeee eeeeeeeeee, eee M8M (8 eM) eee eeeee ee eeeeee eee eeeeeeee. Mee eeeeeee eee eeeeeee ee eeee eee ee eeeee 8 eee ee eeeee eee eeeeee ee eeeee. Meee, eee eeeeeee eee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeee ee eee eeeeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeee eeee eeeee (88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeeee e eeeeee eee. Mee eee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8) ee eeee 888 ee e eeeee; eeeee: 8.88 e (88%); >88% ee; Me 8.88 (MeMMe/eeeeee 8:8); ee 88–88°M; 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M), 8.88 (ee, 8M, M = 88.8, 8.8 Me), 8.88 (ee, 8M, M = 88.8, 88.8 Me), 8.88 (ee, 8M, M = 88.8, 8.8 Me), 8.88–8.88 (e, 8M), 8.88–8.88 (e, 8M), 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me).
References
[525] | Meee, M. M.; Meeeee, M. M.; MeMee, M. M., M. Me. Meee. Mee., (8888) 88, 88. |
[534] | Meeeee, M.; Meeeee, M.; Meeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeee, M., Mee. Meeee. Meeee., (8888) 888, 8888. |
[624] | Meeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeeeeee, M.; Meeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[673] | Meeeeeee, M.; Meeeee, M., Mee. Meeee. Meee. Mee. M, (8888) 88, 8888. |
[674] | Meeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 8888. |
[675] | Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeeee, M. M., M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 8, 8888. |
[676] | Meee’, M. M.; Mee’eeeeeeee, M. M., M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 888. |
[677] | Meeee’eee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 8888. |
[678] | Meeeeeee, M.; Meeeeeee, M.; Mee, M. M.; Meeeeeeeeee, M.; Meeeee, M.; Meeeeeeeee, M.; Meeeeeeee, M., Mee. M. Mee. Meee., (8888) 88, 888. |
[679] | Meeeeeeee, M.; Meëeee, M.; Méeeeeee, M.; Meeeeeeee, M., Meeee. Meeeee., (8888) 88, 888. |
[680] | Meee, M.; Meeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[681] | Meeeeeee, M.; Meeeeeeeeeee, M., Meeeee M. Meee., Meee. M, (8888) 88, 888. |
[682] | Me, M.; Meee, M.; Meee, M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[683] | Meeeeeee, M.; Meeeeee, M.; Meee, M.; Meeeee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
[684] | MeMeeee, M. M.; Meeeee, M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[685] | Me, M.; Meeee, M. M.; Meeee, M. M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
[686] | Meeee, M.; Meeeee, M.; Meeeeeee, M.; Me, M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 888. |
[687] | Me, M.; Me, M.; Mee, M.-M.; Mee, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[688] | Meeeeeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 888. |
[689] | Meeeeee, M. M.; MeMeeeee, M. M.; Meeeeee, M. M.; MeMee, M. M.; Meeeee, M.-M.; Meeeeeee, M. M.; Meee, M., Mee. Meee., (8888) 8, 8888. |
[690] | Me, M.; Me, M.; Mee, M.; Meee, M., Meeeeeeee, (8888), 8888. |
[691] | Me, M.-M.; Mee, M.; Me, M.; Mee, M.; Me, M.-M., Meeeeee, (8888), 8888. |
[692] | Meeeeee, M.; Meeeee, M.; Meeeee, M.; Meeee, M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |