Employing the simple monosilylcopper reagent, Li[PhMe2SiCuI], in 1,4-addition reactions

被引：14

作者：

Dambacher, J ^{[1
]}

Bergdahl, M ^{[1
]}

机构：

[1] San Diego State Univ, Dept Chem, San Diego, CA 92182 USA

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 01期

关键词：

D O I：

10.1039/b210792a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Conjugate addition reactions using the simple Li[PhMe2Si-CuI] reagent to a variety of alpha,beta-unsaturated carbonyl compounds is described; dimethyl sulfide from the purification of CuI plays a key role for very high yields as well as high stereoselectivities in the formation of beta-silyl carbonyl compounds.

引用

页码：144 / 145

页数：2

共 33 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] NEW COPPER CHEMISTRY .15. ORGANOCOPPER REAGENTS IN DIMETHYL SULFIDE [J].

BERTZ, SH ;

DABBAGH, G .

TETRAHEDRON, 1989, 45 (02) :425-434

[3] It's on lithium! An answer to the recent communication which asked the question: 'If the cyano ligand is not on copper, then where is it?' [J].

Bertz, SH ;

Miao, GB ;

Eriksson, M .

CHEMICAL COMMUNICATIONS, 1996, (07) :815-816

[4]

Brook M. A, 2000, SILICON ORGANIC ORGA

[5]

CLARK RD, 1974, TETRAHEDRON LETT, P1713

[6]

Colvin E. W., 1988, SILICON REAGENTS ORG

[7]

Colvin E. W., 1981, SILICON ORGANIC SYNT, P165

[8] NEW METHODS FOR CARBOCYCLIC SNYTHESIS APPLICABLE TO GIBBERELLIC ACIDS - STEREOSELECTIVE INTRODUCTION OF ANGULAR VINYL GROUPING AND PINACOLIC CYCLIZATION OF KETO ALDEHYDES [J].

COREY, EJ ;

CARNEY, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (26) :7318-&

[9] CONJUGATE ADDITION OF THE PHENYLDIMETHYLSILYL GROUP TO ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS USING A SILYLZINCATE IN-PLACE OF THE SILYLCUPRATE [J].

CRUMP, RANC ;

FLEMING, I ;

URCH, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06) :701-706

[10] Iodotrimethylsilane-promoted 1,4-addition of copper acetylides to alpha,beta-unsaturated ketones and aldehydes [J].

Eriksson, M ;

Iliefski, T ;

Nilsson, M ;

Olsson, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :182-187

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