Efficient access to virtually enantiopure alpha-dialkyl-, alpha-acetoxy-, and alpha-acetamido esters

被引：17

作者：

Cave, C ^{[1
]}

LePorhielCastellon, Y ^{[1
]}

Daley, V ^{[1
]}

Riche, C ^{[1
]}

Chiaroni, A ^{[1
]}

dAngelo, J ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(97)10339-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of acyclic chiral beta-enamino ester (S)-1 to alpha-methyl-, alpha-acetoxy-, and alpha-acetamido acrylates 2 gave with good yields, and with de greater than or equal to 95 % the corresponding Michael adducts (S, S)-3. (C) 1997 Published by Elsevier Science Ltd.

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收藏

页码：8703 / 8706

页数：4

相关论文

共 13 条

[1] THE ASYMMETRIC MICHAEL REACTION USING CHIRAL IMINES UNDER NEUTRAL CONDITIONS - STEREOCHEMICAL EVIDENCES IN SUPPORT OF A CYCLIC TRANSITION-STATE [J].

AMBROISE, L ;

DESMAELE, D ;

MAHUTEAU, J ;

DANGELO, J .

TETRAHEDRON LETTERS, 1994, 35 (52) :9705-9708

[2] 5-tert-butylproline [J].

Beausoleil, E ;

LArcheveque, B ;

Belec, L ;

Atfani, M ;

Lubell, WD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9447-9454

[3] SYNTHESIS OF OPTICALLY-ACTIVE MICHAEL ADDUCTS VIA CHIRAL ENAMINES [J].

BRUNNER, H ;

KRAUS, J ;

LAUTENSCHLAGER, HJ .

MONATSHEFTE FUR CHEMIE, 1988, 119 (10) :1161-1167

[4] Condensation of chiral imines and chiral beta-enaminoesters with maleic and citraconic anhydrides [J].

Cave, C ;

Gassama, A ;

Mahuteau, J ;

dAngelo, J ;

Riche, C .

TETRAHEDRON LETTERS, 1997, 38 (27) :4773-4776

[5] METHYL-METHACRYLATE AS ACCEPTOR IN THE ASYMMETRIC MICHAEL REACTION USING CHIRAL BETA-ENAMINOESTERS - SIMULTANEOUS, COMPLETE STEREOCONTROL OF A QUATERNARY CARBON CENTER AND A TERTIARY ONE IN THE BETA-POSITION [J].

CAVE, C ;

DALEY, V ;

DANGELO, J ;

GUINGANT, A .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :79-82

[6] Stereochemical aspects in the asymmetric Michael addition of chiral imines to substituted electrophilic alkenes [J].

Cave, C ;

Desmaele, D ;

dAngelo, J ;

Riche, C ;

Chiaroni, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4361-4368

[7]

DANGELO J, 1998, IN PRESS HETEROCYCLE, V47

[8] ALKYLATION OF ALLYLIC DERIVATIVES .7. STEREOCHEMISTRY OF ALKYLATION OF THE ISOMERIC TRANS-ALPHA,GAMMA-METHYL(PHENYL)ALLYL ACETATES WITH LITHIUM DIALKYLCUPRATES AND ALKYLCYANOCUPRATES [J].

GOERING, HL ;

TSENG, CC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :3986-3990

[9] AN ASYMMETRIC-SYNTHESIS OF (R)-(+)-2-NONYL-2-(CARBOMETHOXY)-CYCLOPENTANONE, A KNOWN PRECURSOR OF THE ANTIBIOTIC (-)-MALYNGOLIDE [J].

GUINGANT, A .

TETRAHEDRON-ASYMMETRY, 1991, 2 (06) :415-418

[10] ASYMMETRIC NUCLEOPHILIC-ADDITION OF CHIRAL BETA-ENAMINO ESTERS TO ACRYLONITRILE [J].

GUINGANT, A ;

HAMMAMI, H .

TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :25-26