Iodine as novel reagent for the 1,2-addition of trimethylsilyl cyanide to ketones including α,β-unsaturated ketones

被引：96

作者：

Yadav, JS ^{[1
]}

Reddy, BVS ^{[1
]}

Reddy, MS ^{[1
]}

Prasad, AR ^{[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：

ketones; trimethylsiyl cyanide; iodine; alpha-cyanohydrins;

D O I：

10.1016/S0040-4039(02)02321-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Molecular iodine is found to catalyze efficiently the addition of trimethylsilyl cyanide to a range of simple and functionalized ketones under very mild and convenient conditions to afford the corresponding cyanohydrin trimethylsilyl ethers in excellent yields in a short reaction period with high selectivity. a,P-Unsaturated ketones selectively afford the corresponding 1,2-adducts without the formation of 1,4-adducts under similar reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9703 / 9706

页数：4

共 27 条

[1]

[Anonymous], J CHEM SOC P1

[2] Indium tribromide:: a highly effective catalyst for the addition of trimethylsilyl cyanide to α-hetero-substituted ketones [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Umani-Ronchi, A .

TETRAHEDRON LETTERS, 2001, 42 (16) :3041-3043

[3]

Colvin E. W., 1981, SILICON ORGANIC SYNT, P97

[4]

Curini M, 1999, SYNLETT, P315

[5] Iodine as acetylation catalyst in the preparation of 1,1-diacetates from aldehydes [J].

Deka, N ;

Kalita, DJ ;

Borah, R ;

Sarma, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1563-1564

[6] An efficient synthesis of dinitrile derivatives by the reaction of oxime esters or acid anhydrides with cyanotrimethylsilane catalyzed by La(O(i)Pr)3 [J].

Fujii, A ;

Sakaguchi, S ;

Ishii, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6209-6212

[7]

GASSMAN PG, 1978, TETRAHEDRON LETT, P3773

[8] ADDITION OF TERT-BUTYLDIMETHYLSILYL OR TERT-BUTYLDIPHENYLSILYL CYANIDE TO HINDERED KETONES [J].

GOLINSKI, M ;

BROCK, CP ;

WATT, DS .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :159-164

[9] ADDITION OF TRIMETHYLSILYL CYANIDE TO ALPHA-SUBSTITUTED KETONES - CATALYST EFFICIENCY [J].

GREENLEE, WJ ;

HANGAUER, DG .

TETRAHEDRON LETTERS, 1983, 24 (42) :4559-4560

[10] Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications [J].

Gregory, RJH .

CHEMICAL REVIEWS, 1999, 99 (12) :3649-3682

← 1 2 3 →