REGIOSPECIFIC OPENING OF 1,2-EPOXIDES WITH ACETONE CYANOHYDRIN UNDER MILDLY BASIC CONDITIONS

被引：41

作者：

MITCHELL, D

KOENIG, TM

机构：

[1] Lilly Research Laboratories, Eli Lilly and Company Lilly Corporate Center, Indianapolis

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(00)92067-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetone cyanohydrin With stoichiometric triethylamine opens epoxides regiospecifically to give beta-hydroxy nitriles. As expected, addition of cyanide occurs at the least substituted carbon.

引用

页码：3281 / 3284

页数：4

共 10 条

[1] ARENESULFONATE DERIVATIVES OF HOMOCHIRAL GLYCIDOL - VERSATILE CHIRAL BUILDING-BLOCKS FOR ORGANIC-SYNTHESIS [J].

KLUNDER, JM ;

ONAMI, T ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1295-1304

[2] PARA-NITROBENZOATE ESTERS OF EPOXY ALCOHOLS - CONVENIENT SYNTHONS FOR WATER-SOLUBLE EPOXY ALCOHOLS [J].

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) :667-671

[3]

KOENIG KE, 1974, TETRAHEDRON LETT, V26, P2275

[4]

LIOTTA CL, 1977, TETRAHEDRON LETT, V13, P1117

[5] HYDROCYANATION .10. CLEAVAGE OF EPOXIDES WITH HYDROGEN CYANIDE AND TRIETHYLALUMINIUM AND WITH DIETHYLALUMINIUM CYANIDE [J].

NAGATA, W ;

YOSHIOKA, M ;

OKUMURA, T .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (17) :2365-&

[6] ACETONE CYANOHYDRIN, A CONVENIENT FORMYLATION REAGENT FOR ARENES [J].

RAHM, A ;

GUILHEMAT, R ;

PEREYRE, M .

SYNTHETIC COMMUNICATIONS, 1982, 12 (06) :485-487

[7] SYNTHETIC METHODS AND REACTIONS .144. REGIOSPECIFIC AND CHEMOSELECTIVE RING-OPENING OF EPOXIDES WITH TRIMETHYLSILYL CYANIDE POTASSIUM CYANIDE 18-CROWN-6 COMPLEX [J].

SASSAMAN, MB ;

PRAKASH, GK ;

OLAH, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2016-2018

[8] ALIPHATIC NITRILES FROM ALKYL CHLORIDES [J].

SMILEY, RA ;

ARNOLD, C .

JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (02) :257-258

[9]

SUGITA K, 1990, CHEM LETT, V3, P481

[10]

ZUBRICK JW, 1975, TETRAHEDRON LETT, P71

← 1 →