DIASTEREOSELECTIVE HETEROATOM-DIRECTED CONJUGATE ADDITION OF SILYLCUPRATE REAGENTS TO UNSATURATED CARBONYLS - A STEREOSELECTIVE ROUTE TO BETA-CARBONYL SILOXANES

被引：26

作者：

HALE, MR ^{[1
]}

HOVEYDA, AH ^{[1
]}

机构：

[1] BOSTON COLL,MERKERT CHEM CTR,DEPT CHEM,CHESTNUT HILL,MA 02167

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 16期

关键词：

D O I：

10.1021/jo00095a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Directed conjugate addition of the silylcuprate reagent lithium bis[diphenyl(diethylamino)silyl]-cuprate ((Ph(2)(Et(2)N)Si)(2)CuLi) to unsaturated esters and ketones is reported. The stereochemical course of the reaction can be-controlled by the presence of an appropriately disposed internal Lewis basic functionality, affording the corresponding beta-hydroxysilyl carbonyls with good to excellent levels of diastereoselection (e.g., 3b --> 4b).

引用

页码：4370 / 4374

页数：5

共 34 条

[1] THE CONJUGATE ADDITION OF A SILYL GROUP TO ENONES AND ITS REMOVAL WITH COPPER(II) BROMIDE - A PROTECTING GROUP FOR THE ALPHA-BETA-UNSATURATION OF ALPHA-BETA-UNSATURATED KETONES [J].

AGER, DJ ;

FLEMING, I ;

PATEL, SK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2520-2526

[2] STRUCTURE OF A POLYMERIC COMPLEX BETWEEN ACRYLALDEHYDE AND COPPER(I) CHLORIDE [J].

ANDERSSON, S ;

HAKANSSON, M ;

JAGNER, S ;

NILSSON, M ;

ULLENIUS, C ;

URSO, F .

ACTA CHEMICA SCANDINAVICA SERIES A-PHYSICAL AND INORGANIC CHEMISTRY, 1986, 40 (01) :58-62

[3] ASYMMETRIC CATALYSIS - PRODUCTION OF CHIRAL DIOLS BY ENANTIOSELECTIVE CATALYTIC INTRAMOLECULAR HYDROSILATION OF OLEFINS [J].

BERGENS, SH ;

NOHEDA, P ;

WHELAN, J ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2121-2128

[4]

BERNHARD W, 1984, J CHEM SOC CHEM COMM, P29

[5] NEW COPPER CHEMISTRY .16. MECHANISM OF ORGANOCUPRATE CONJUGATE ADDITION - OBSERVATION OF CUPRATE OLEFIN COMPLEXES AND LI-COORDINATED INTERMEDIATES IN THE REACTION OF LITHIUM DIMETHYLCUPRATE(I) WITH 10-METHYL-DELTA-1,9-2-OCTALONE [J].

BERTZ, SH ;

SMITH, RAJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8276-8277

[6] CONFORMATIONAL-ANALYSIS OF CHIRAL ALKENES AND OXONIUM IONS - ABINITIO MOLECULAR-ORBITAL CALCULATIONS AND AN IMPROVED MM2 FORCE-FIELD [J].

BROEKER, JL ;

HOFFMANN, RW ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5006-5017

[7] EPOXIDATION OF ALLYLIC ALCOHOLS WITH PEROXY-ACIDS - ATTEMPTS TO DEFINE TRANSITION STATE GEOMETRY [J].

CHAMBERL.P ;

ROBERTS, ML ;

WHITHAM, GH .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (07) :1374-&

[8] A SYNTHESIS OF THE PRELOG-DJERASSI LACTONE USING OPEN-CHAIN STEREOCONTROL BASED ON ALLYLSILANE CHEMISTRY [J].

CHOW, HF ;

FLEMING, I .

TETRAHEDRON LETTERS, 1985, 26 (03) :397-400

[9] ADDITION OF ME2CULI TO ORTHO-SUBSTITUTED METHYL CINNAMATES - AN NMR-STUDY OF THE PI-COMPLEX FORMATION [J].

CHRISTENSON, B ;

OLSSON, T ;

ULLENIUS, C .

TETRAHEDRON, 1989, 45 (02) :523-534

[10]

CHRISTENSON B, 1987, CHEM SCRIPTA, V27, P511

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