FACILE CONVERSION OF EPOXIDES TO BETA-HYDROXY NITRILES UNDER ANHYDROUS CONDITIONS WITH LITHIUM CYANIDE

被引:46
作者
CIACCIO, JA
STANESCU, C
BONTEMPS, J
机构
[1] Department of Chemistry, Fordham University, Bronx
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)91639-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Functionalized epoxides are easily and efficiently converted to beta-hydroxy nitriles in good yield with high regio- and stereoselectivity upon treatment with lithium cyanide in refluxing anhydrous THF. The conditions described permit a one-pot conversion of epoxide to 1,3-amino alcohol via hydride reduction of the nitrile.
引用
收藏
页码:1431 / 1434
页数:4
相关论文
共 21 条
[1]   SELECTIVE TRANSFORMATION OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-1 [J].
BEHRENS, CH ;
KO, SY ;
SHARPLESS, KB ;
WALKER, FJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5687-5696
[2]  
BOIKO IP, 1977, ZH ORG KHIM+, V13, P327
[3]   TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].
CARON, M ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560
[4]   EASY DIRECT STEREOSELECTIVE AND REGIOSELECTIVE FORMATION OF BETA-HYDROXY NITRILES BY REACTION OF 1,2-EPOXIDES WITH POTASSIUM CYANIDE IN THE PRESENCE OF METAL-SALTS [J].
CHINI, M ;
CROTTI, P ;
FAVERO, L ;
MACCHIA, F .
TETRAHEDRON LETTERS, 1991, 32 (36) :4775-4778
[5]   EPOXIDE-OPENING WITH TRIMETHYLSILYL CYANIDE CATALYZED BY TETRAISOPROPYL ORTHOTITANATE [J].
EMZIANE, M ;
LHOSTE, P ;
SINOU, D .
JOURNAL OF MOLECULAR CATALYSIS, 1988, 49 (01) :L23-L25
[6]  
FULOP F, 1991, SYNTHESIS-STUTTGART, P43
[7]   NONAQUEOUS CYANATION OF HALIDES USING LITHIUM CYANIDE [J].
HARUSAWA, S ;
YONEDA, R ;
OMORI, Y ;
KURIHARA, T .
TETRAHEDRON LETTERS, 1987, 28 (36) :4189-4190
[8]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .39. A NOVEL SYNTHESIS OF ALPHA,BETA-UNSATURATED NITRILES FROM AROMATIC KETONES VIA CYANOPHOSPHATES [J].
HARUSAWA, S ;
YONEDA, R ;
KURIHARA, T ;
HAMADA, Y ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1984, 25 (04) :427-428
[9]   ENZYMATIC RESOLUTIONS OF CYCLIC AMINO ALCOHOL PRECURSORS [J].
HONIG, H ;
SEUFERWASSERTHAL, P ;
FULOP, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12) :2341-2345
[10]   REACTION OF CYANOTRIMETHYLSILANE WITH OXIRANES - EFFECTS OF CATALYSTS OR MEDIATORS ON REGIOSELECTIVITY AND AMBIDENT CHARACTER [J].
IMI, K ;
YANAGIHARA, N ;
UTIMOTO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1013-1016