CHEMISTRY OF DIORGANOCUPRATES CONTAINING FUNCTIONALIZED LIGANDS .2. METHODOLOGY FOR CONJUGATE ADDITION OF SYNTHETIC EQUIVALENTS OF ENOLATES AND ACYL ANIONS

被引：46

作者：

BOECKMAN, RK

BRUZA, KJ

机构：

[1] Department of Chemistry, Wayne State University, Detroit

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 26期

关键词：

D O I：

10.1021/jo00394a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methodology is described by which several classes of masked synthons, the synthetic equivalents of acyl anions and enolates, can be rendered reactive as ligands in the corresponding diorganocuprate complexes. Vinyl ethers and vinylsilanes were studied, and a comparison of their reactivities, stabilities and unmasking characteristics is given. The two classes of reagents prove nicely complementary in terms of their spectrum of reactivity, selectivity, and ease in unmasking. © 1979, American Chemical Society. All rights reserved.

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页码：4781 / 4788

页数：8

相关论文

共 38 条

[1] ALPHA-METHOXYVINYLLITHIUM AND RELATED METALATED ENOL ETHERS - PRACTICAL REAGENTS FOR NUCLEOPHILIC ACYLATION [J].

BALDWIN, JE ;

HOFLE, GA ;

LEVER, OW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (22) :7125-7127

[2] STEREOCHEMISTRY OF ADDITION OF SILICOCHLOROFORM TO ACETYLENES - A COMPARISON OF CATALYST SYSTEMS [J].

BENKESER, RA ;

BURROUS, ML ;

SWISHER, JV ;

NELSON, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (21) :4385-&

[3]

Boeckman R. K., 1978, ORG SYNTH, V58, P152

[4]

BOECKMAN RK, 1977, TETRAHEDRON LETT, P4187

[5] PREPARATION AND REACTIONS OF DIORGANOCUPRATE REAGENTS DERIVED FROM 2-LITHIO-3,3-DIETHOXYPROPENE - FUNCTIONALIZED REAGENTS FOR TRANSFER OF AN ALPHA-ACROLEIN CARBANION EQUIVALENT [J].

BOECKMAN, RK ;

RAMAIAH, M .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (09) :1581-1586

[6] ADDITION OF HYDROGEN BROMIDE TO 1-TRIMETHYLSILYL-1-ALKYNES - CONVENIENT SYNTHESIS OF 2-BROMO-1-ALKENES [J].

BOECKMAN, RK ;

BLUM, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (22) :3307-3308

[7]

BOECKMAN RK, 1974, TETRAHEDRON LETT, P3365

[8] COPPER ATE COMPLEXES OF ALPHA-ETHOXYVINYL-LITHIUM - REAGENTS FOR COUPLING AND 1,4 ADDITION OF A MASKED ACYL ANION [J].

BOECKMAN, RK ;

BRUZA, KJ ;

BALDWIN, JE ;

LEVER, OW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (13) :519-520

[9] MIXED CUPRATE REAGENTS OF TYPE R1R2CULI WHICH ALLOW SELECTIVE GROUP TRANSFER [J].

COREY, EJ ;

BEAMES, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) :7210-&

[10] HYDROXYPROPYLATION [J].

EATON, PE ;

COOPER, GF ;

JOHNSON, RC ;

MUELLER, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (12) :1947-&

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