Enantioselective synthesis of homologous methyl-substituted bicyclic enones through Michael-type alkylation of chiral imines

被引：6

作者：

Goubaud, V ^{[1
]}

Azerad, R ^{[1
]}

机构：

[1] UNIV PARIS 05,CHIM & BIOCHIM PHARMACOL & TOXICOL LAB,URA 400 CNRS,F-75270 PARIS 06,FRANCE

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 05期

关键词：

D O I：

10.1080/00397919608003696

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of 4a-methyl-substituted bicyclic enones iri high enantiomeric purity is described, involving a Michael alkylation of (R)- or (S)-1-phenylethyl imines of the corresponding (+/-)-2-methylcyclopentanone, 2-methylcyclohexanone, 2-methylcycloheptanone, and 2-methylcyclooctanone with methyl vinyl ketone.

引用

页码：915 / 922

页数：8

共 24 条

[21] Synthesis of Functionalized Indoles with a Trifluoromethyl-Substituted Stereogenic Tertiary Carbon Atom Through an Enantioselective Friedel-Crafts Alkylation with β-Trifluoromethyl-α,β-enones
Blay, Gonzalo
Fernandez, Isabel
Carmen Munoz, M.
Pedro, Jose R.
Vila, Carlos
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) : 9117 - 9122
[22] Enantioselective synthesis of 2-indolyl methanamine derivatives through disulfonimide-catalyzed Friedel-Crafts C2-alkylation of 3-substituted indoles with imines
Sun, Peng
Jia, Zi-Hao
Tang, Li
Zheng, Hao
Li, Zhang-Rui
Chen, Ling-Yan
Li, Ya
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (09) : 1916 - 1925
[23] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED BETA-AMINO ACID-ESTERS BY TANDEM MICHAEL-ADDITION ALPHA-ALKYLATION WITH TMS-SAMP AS CHIRAL EQUIVALENT OF AMMONIA
ENDERS, D
BETTRAY, W
RAABE, G
RUNSINK, J
SYNTHESIS-STUTTGART, 1994, : 1322 - 1326
[24] Enantioselective syntheses of (2S,4aS,8aR)-1,1,4a-trimethyldecahydronaphthalen-2-ol[(-)-TMD], (4aS,8aR)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one, and (-)-Polywood(R), through Michael-type reaction of chiral imines
Jabin, I
Revial, G
Melloul, K
Pfau, M
TETRAHEDRON-ASYMMETRY, 1997, 8 (07) : 1101 - 1109

← 1 2 3 →