Enantioselective 1,4-addition of aryllithium reagents to α,β-unsaturated tert-butyl esters in the presence of chiral additives

被引：46

作者：

Xu, F ^{[1
]}

Tillyer, RD ^{[1
]}

Tschaen, DM ^{[1
]}

Grabowski, EJJ ^{[1
]}

Reider, PJ ^{[1
]}

机构：

[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(98)00157-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of t-BuLi with a mixture of aryl bromide and chiral diamine, amino ether or diether, in toluene at -78 degrees C provided chiral aryllithium complexes efficiently. Reaction of these aryllithium complexes with alpha,beta-unsaturated tert-butyl esters afforded the 1,4-addition products in up to 88% ee. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：1651 / 1655

页数：5

相关论文

共 17 条

[1] DIASTEREOSELECTIVE CONJUGATE ADDITION WITH ACETALS, OXAZOLIDINES AND IMIDAZOLIDINES AS CHIRAL AUXILIARIES [J].

ALEXAKIS, A ;

SEDRANI, R ;

MANGENEY, P ;

NORMANT, JF .

TETRAHEDRON LETTERS, 1988, 29 (35) :4411-4414

[2] STERIC CONSEQUENCE OF THE DIASTEREOSELECTIVE ADDITION OF CHIRAL LITHIUM 2-(1-DIMETHYLAMINOETHYL)PHENYL CUPRATES TO SOME ENONES [J].

ANDERSSON, S ;

JAGNER, S ;

NILSSON, M ;

URSO, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 301 (02) :257-267

[3] Enantioselective conjugate additions of organolithiums to BHA enoates mediated by a chiral ligand [J].

Asano, Y ;

Iida, A ;

Tomioka, K .

TETRAHEDRON LETTERS, 1997, 38 (52) :8973-8976

[4] STEREOSELECTIVE ADDITION OF R2CULI TO ORTHO-SUBSTITUTED METHYL CINNAMATES - INTRAMOLECULAR ASSISTANCE AND SOLVENT EFFECTS [J].

CHRISTENSON, B ;

HALLNEMO, G ;

ULLENIUS, C .

TETRAHEDRON, 1991, 47 (26) :4739-4752

[5]

COREY EJ, 1994, TETRAHEDRON LETT, V35, P5371

[6]

FREY LF, 1998, IN PRESS J ORG CHEM

[7]

JOHNSON RE, 1991, Patent No. 5098901

[8]

JONES G, 1971, J MED CHEM, V14, P161

[9] STEREOSELECTIVITY IN THE TRANSFER OF THE 2-(1-DIMETHYLAMINOETHYL)PHENYL GROUP, RSTAR, FROM LIRSTAR2CU AND LI(RSTAR)(2-THIENYL)CU TO ENONES [J].

MALMBERG, H ;

NILSSON, M ;

ULLENIUS, C .

TETRAHEDRON LETTERS, 1982, 23 (37) :3823-3826

[10] NEW CALMODULIN ANTAGONISTS OF THE DIPHENYLALKYLAMINE TYPE .1. BIOLOGICAL-ACTIVITY, SAR AND THE ROLE OF LIPOPHILICITY [J].

MANNHOLD, R ;

CALDIROLA, P ;

BIJLOO, GJ ;

TIMMERMAN, H .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (09) :727-734