3-aminopyrrolidine lithium amide in enantioselective addition of organolithium compounds onto aromatic aldehydes

被引：49

作者：

Corruble, A

Valnot, JY

Maddaluno, J

Duhamel, P

机构：

[1] CNRS,URA 464,FAC SCI & TECH,F-76821 MONT ST AIGNAN,FRANCE

[2] UNIV ROUEN,IRCOF,F-76821 MONT ST AIGNAN,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(97)00114-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New N,N'-disubstituted-3-aminopyrrolidines lithium amides have been used as chiral auxiliaries in the asymmetric condensation of n-butyllithium onto aromatic aldehydes, leading to e.e.s up to 73%. (C) 1997 Elsevier Science Ltd.

引用

页码：1519 / 1523

页数：5

共 34 条

[1] ASYMMETRIC CONJUGATE ADDITIONS TO CHIRAL BICYCLIC LACTAMS - A STEREOSELECTIVE GENERAL-SYNTHESIS OF CHIRAL 3-AMINOPYRROLIDINES [J].

ANDRES, CJ ;

LEE, PH ;

NGUYEN, TH ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3189-3193

[2]

BARELLE M, 1990, J CHEM RES M, P701

[3] Control of the enantiochemistry of electrophilic substitutions of N-pivaloyl-alpha-lithio-o-ethylaniline: Stereoinformation transfer based on the method of organolithium formation [J].

Basu, A ;

Beak, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) :1575-1576

[4]

BATH KL, 1985, SYNTHETIC COMMUN, V15, P587

[5]

Bowers-Nemia, 1983, SYNTHETIC COMMUN, V13, P1117

[6] OPTICALLY-ACTIVE AMINES .36. APPLICATION OF THE BENZENE CHIRALITY RULE TO RING-SUBSTITUTED MANDELIC-ACIDS [J].

COLON, DF ;

PICKARD, ST ;

SMITH, HE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2322-2326

[7] THE INSITU PROTECTION OF ALDEHYDES VIA ALPHA-AMINO ALKOXIDES [J].

COMINS, DL ;

BROWN, JD .

TETRAHEDRON LETTERS, 1981, 22 (42) :4213-4216

[8] A ONE-POT ORTHO-ALKYLATION OF AROMATIC-ALDEHYDES [J].

COMINS, DL ;

BROWN, JD ;

MANTLO, NB .

TETRAHEDRON LETTERS, 1982, 23 (39) :3979-3982

[9]

COMINS DL, 1992, SYNLETT, P615

[10]

CORRUBLE A, UNPUB

← 1 2 3 4 →