1,4-Conjugate addition of allyltrimethylsilane to α,β-unsaturated ketones

被引：47

作者：

Yadav, JS ^{[1
]}

Reddy, BVS ^{[1
]}

Sadasiv, K ^{[1
]}

Satheesh, G ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 52期

关键词：

Michael addition; alpha; beta-unsaturated ketones; iodine catalysis; 1,4-adducts;

D O I：

10.1016/S0040-4039(02)02373-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha,beta-Unsaturated ketones smoothly undergo conjugate addition with allyltrimethylsilane in the presence of a catalytic amount of elemental iodine under very mild and convenient conditions to afford the corresponding Michael adducts in high yields with high selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9695 / 9697

页数：3

共 16 条

[1] [Anonymous], J CHEM SOC P1
[2] Colvin E. W., 1981, SILICON ORGANIC SYNT, P97
[3] Fleming I., 1989, ORG REACTIONS, V37, P57
[4] CHEMISTRY OF ORGANOSILICON COMPOUNDS .99. CONJUGATE ADDITION OF ALLYLSILANES TO ALPHA, BETA-ENONES - NEW METHOD OF STEREOSELECTIVE INTRODUCTION OF ANGULAR ALLYL GROUP IN FUSED CYCLIC ALPHA, BETA-ENONES
HOSOMI, A
SAKURAI, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (05) : 1673 - 1675
[5] CHARACTERISTICS IN THE REACTIONS OF ALLYLSILANES AND THEIR APPLICATIONS TO VERSATILE SYNTHETIC EQUIVALENTS
HOSOMI, A
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (05) : 200 - 206
[6] Iodine-catalyzed mild and efficient tetrahydropyranylation/depyranylation of alcohols
Kumar, HMS
Reddy, BVS
Reddy, EJ
Yadav, JS
[J]. CHEMISTRY LETTERS, 1999, (09) : 857 - 858
[7] USES OF SILICON-CONTAINING COMPOUNDS IN THE SYNTHESIS OF NATURAL-PRODUCTS
LANGKOPF, E
SCHINZER, D
[J]. CHEMICAL REVIEWS, 1995, 95 (05) : 1375 - 1408
[8] The catalytic Sakurai reaction
Lee, PH
Lee, K
Sung, SY
Chang, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) : 8646 - 8649
[9] Studies on the reactions of α,β-enones with allyl indium reagent;: effects of TMSCl as promoter on regioselectivity
Lee, PH
Ahn, H
Lee, K
Sung, SY
Kim, S
[J]. TETRAHEDRON LETTERS, 2001, 42 (01) : 37 - 39
[10] CONJUGATE ADDITION-REACTIONS OF ALLYLIC COPPER SPECIES DERIVED FROM GRIGNARD-REAGENTS - SYNTHETIC AND SPECTROSCOPIC ASPECTS
LIPSHUTZ, BH
HACKMANN, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) : 7437 - 7444

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