Conjugate addition of alpha-alkoxystannanes via in situ transmetalation using catalytic CuCN

被引：11

作者：

Bhatt, RK

Ye, JH

Falck, JR

机构：

[1] UNIV TEXAS,SW MED CTR,DEPT MOLEC GENET,DALLAS,TX 75235

[2] UNIV TEXAS,SW MED CTR,DEPT PHARMACOL,DALLAS,TX 75235

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 22期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(96)00710-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic CuCN mediates the in situ transmetalation of alpha-thionocarbamoyl stannanes and subsequent conjugate addition to alpha,beta-unsaturated carbonyls in the presence of chlorotrimethlysilane at or a little above room temperature. Copyright (C) 1996 Elsevier Science Ltd

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页码：3811 / 3814

页数：4

相关论文

共 19 条

[1] ADDITIONS OF ORGANOCOPPER REAGENTS TO ALLYLIC EPOXIDES [J].

ANDERSON, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (16) :4978-&

[2] INSITU CUPRATE FORMATION VIA TRANSMETALATION BETWEEN VINYLSTANNANES AND HIGHER-ORDER CYANOCUPRATES [J].

BEHLING, JR ;

BABIAK, KA ;

NG, JS ;

CAMPBELL, AL ;

MORETTI, R ;

KOERNER, M ;

LIPSHUTZ, BH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2641-2643

[3] RULES FOR RING-FUSION GEOMETRY AND THE PREPARATION OF TRANS-FUSED OR CIS-FUSED BICYCLIC COMPOUNDS BY RADICAL CLOSURE [J].

CLIVE, DLJ ;

CHESHIRE, DR ;

SET, L .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (05) :353-355

[4] TIN-COPPER TRANSMETALATION - CROSS-COUPLING OF ALPHA-HETEROATOM-SUBSTITUTED ALKYLTRIBUTYLSTANNANES WITH ORGANOHALIDES [J].

FALCK, JR ;

BHATT, RK ;

YE, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :5973-5982

[5] ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].

FARINA, V ;

KAPADIA, S ;

KRISHNAN, B ;

WANG, CJ ;

LIEBESKIND, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5905-5911

[6] AMELIORATION OF THE CONJUGATE ADDITION CHEMISTRY OF ALPHA-ALKOXYCOPPER REAGENTS - APPLICATION TO THE STEREOSPECIFIC SYNTHESIS OF C-GLYCOSIDES [J].

HUTCHINSON, DK ;

FUCHS, PL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (16) :4930-4939

[7] NUCLEOPHILIC REACTIVITY OF ZINC AND COPPER CARBENOIDS .2. [J].

KNOCHEL, P ;

CHOU, TS ;

CHEN, HG ;

YEH, MCP ;

ROZEMA, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5202-5204

[8]

KNOCHEL P, 1990, J ORG CHEM, V55, P4791

[9] CONFIGURATIONALLY FIXED ALPHA-ALKOXYORGANOCOPPER REAGENTS - 1,4-ADDITION OF CYCLIC ENANTIOPURE TRANSFERABLE LIGANDS WITH COMPLETE RETENTION OF CONFIGURATION [J].

LINDERMAN, RJ ;

GRIEDEL, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5491-5493

[10] A REACTIVITY UMPOLUNG ROUTE TO CYCLIC HOMOENOLATE ALDOL PRODUCTS VIA ALPHA-ALKOXYORGANOCUPRATE CONJUGATE ADDITIONS [J].

LINDERMAN, RJ ;

GODFREY, A ;

HORNE, K .

TETRAHEDRON LETTERS, 1987, 28 (34) :3911-3914