Ring-opening of epoxyalcohols by diethylaluminium cyanide. Regio- and stereoselective synthesis of 1-cyano-2,3-diols

被引：23

作者：

Benedetti, F ^{[1
]}

Berti, F ^{[1
]}

Norbedo, S ^{[1
]}

机构：

[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 05期

关键词：

aluminium and compounds; cyano compounds; epoxides; diols;

D O I：

10.1016/S0040-4039(98)02520-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diethylaluminium cyanide is a highly selective reagent for the ring opening of 2,3-epoxyalcohols under mild conditions; the reaction takes place at C-3, with inversion of configuration, to give 1-cyano-2,3-diols. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1041 / 1044

页数：4

相关论文

共 25 条

[1] Molecular recognition of protein-ligand complexes: Applications to drug design [J].

Babine, RE ;

Bender, SL .

CHEMICAL REVIEWS, 1997, 97 (05) :1359-1472

[2] DESIGN AND SYNTHESIS OF 6-ALPHA-SUBSTITUTED 2-BETA,4-ALPHA-DIHYDROXY-1-BETA-PHOSPHORYLOXYCYCLOHEXANES, POTENT INHIBITORS OF INOSITOL MONOPHOSPHATASE [J].

BAKER, R ;

CARRICK, C ;

LEESON, PD ;

LENNON, IC ;

LIVERTON, NJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) :298-300

[3] Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide [J].

Benedetti, F ;

Berti, F ;

Norbedo, S .

TETRAHEDRON LETTERS, 1998, 39 (43) :7971-7974

[4] Versatile and stereoselective synthesis of diamino diol dipeptide isosteres, core units of pseudopeptide HIV protease inhibitors [J].

Benedetti, F ;

Miertus, S ;

Norbedo, S ;

Tossi, A ;

Zlatoidzky, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9348-9353

[5] REGIOSELECTIVE AZIDE OPENING OF 2,3-EPOXY ALCOHOLS BY [TI(O-I-PR)2(N3)2] - SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

CARON, M ;

CARLIER, PR ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5185-5187

[6] 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

[7] STEREOSELECTIVE METHYLATION OF BETA-HYDROXYLACTONE DIANIONS [J].

CHAMBERLIN, AR ;

DEZUBE, M .

TETRAHEDRON LETTERS, 1982, 23 (30) :3055-3058

[8] REGIOCONTROL IN NUCLEOPHILIC RING-OPENING OF CHIRAL EPOXIDES OF CHEMOENZYMATIC ORIGIN [J].

GUANTI, G ;

MERLO, V ;

NARISANO, E .

TETRAHEDRON, 1994, 50 (42) :12245-12258

[9] THE SYNTHETIC METHODOLOGY OF NONRACEMIC GLYCIDOL AND RELATED 2,3-EPOXY ALCOHOLS [J].

HANSON, RM .

CHEMICAL REVIEWS, 1991, 91 (04) :437-475

[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