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

[1] Enantioselective synthesis of homologous methyl-substituted bicyclic enones through Michael-type alkylation of chiral imines
Lab. Chim./Biochim. Pharmacol./T., URA 400 CNRS, Univ. Rene Descartes-Paris V, 45 rue des Saints-Pères, 75270-PARIS Cedex 06, France
SYNTH. COMMUN., 5 (915-922):
[2] ENANTIOSELECTIVE SYNTHESIS OF QUATERNARY CARBON CENTERS THROUGH MICHAEL-TYPE ALKYLATION OF CHIRAL IMINES
PFAU, M
REVIAL, G
GUINGANT, A
DANGELO, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (01) : 273 - 274
[3] ENANTIOSELECTIVE SYNTHESIS OF RING-C AROMATIC STEROIDS BY ASYMMETRIC MICHAEL-TYPE ALKYLATION OF CHIRAL IMINES
VOLPE, T
REVIAL, G
PFAU, M
DANGELO, J
TETRAHEDRON LETTERS, 1987, 28 (21) : 2367 - 2370
[4] Stereocontrolled elaboration of quaternary carbon centers through the asymmetric Michael-Type alkylation of chiral imines secondary enamines: Enantioselective synthesis of (+)-vincamine
Desmaele, D
Mekouar, K
dAngelo, J
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12): : 3890 - 3901
[5] ASYMMETRIC　MICHAEL－TYPE　ALKYLATION　OF　CHIRAL　IMINES　DIASTEREOSELECTIVE　SYNTHESIS　OF（＋）－α－CYPERONE　AND　（－）－10－EPI－α－CYPERONE
Zhao Ming XIONG
Jiong YANG
Yu Lin LI
Ren An LIAO
Zheng Ming LI(State Key Laboratory of Applied Organic Chemistry and Instute of Organic Chemistry
ChineseChemicalLetters, 1996, (08) : 695 - 696
[6] Stereocontrolled elaboration of quaternary carbon centers involving the asymmetric Michael-type alkylation of chiral imines: An efficient enantioselective access to (+)-vincamine
Alves, JCF
Simas, ABC
Costa, PRR
dAngelo, J
TETRAHEDRON-ASYMMETRY, 1997, 8 (12) : 1963 - 1966
[7] Enantioselective synthesis of (+)-α-vetivone through the Michael reaction of chiral imines
Revial, G
Jabin, I
Pfau, M
TETRAHEDRON-ASYMMETRY, 2000, 11 (24) : 4975 - 4983
[8] ASYMMETRIC MICHAEL-TYPE ALKYLATION OF CHIRAL IMINES - ENANTIOSELECTIVE SYNTHESES OF (-)-GEOSMIN AND 2 OTHER RELATED NATURAL TERPENES, AS WELL AS ENANT-(+)-GEOSMIN
REVIAL, G
TETRAHEDRON LETTERS, 1989, 30 (31) : 4121 - 4124
[9] Intramolecular Michael-type additions to vinyl bissulfoxides: Enantioselective synthesis of chiral aldehydes
Gehring, Timo
Podlech, Joachim
Rothenberger, Alexander
SYNTHESIS-STUTTGART, 2008, (15): : 2476 - 2487
[10] SYNTHESIS OF ANGULAR METHYL-SUBSTITUTED BICYCLIC ENONES VIA A UNIQUE REGIOSELECTIVE ENAMINE ANNULATION REACTION
KONST, WMB
WITTEVEEN, JG
BOELENS, H
TETRAHEDRON, 1976, 32 (12) : 1415 - 1421

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