Syntheses with organoboranes .6. Kinetic resolution of vinylic epoxides by the reduction with chiral dialkylboranes

被引：12

作者：

Zaidlewicz, M

Krzeminski, M

机构：

[1] Faculty of Chemistry, Nicolaus Copernicus University

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 39期

关键词：

D O I：

10.1016/0040-4039(96)01559-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of enantiomerically enriched 2-vinyloxirane and monoepoxides of 1,3-cycloalkadienes by kinetic resolution of racemates with Ipc(2)BH, 2-(d)Icr(2)BH and 4-(d)Icr(2)BH of high enantiomeric purity is described. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

收藏

页码：7131 / 7134

页数：4

相关论文

共 20 条

[1] CYCLOHEXENYL NUCLEOSIDES AND RELATED-COMPOUNDS [J].

ARANGO, JH ;

GEER, A ;

RODRIGUEZ, J ;

YOUNG, PE ;

SCHEINER, P .

NUCLEOSIDES & NUCLEOTIDES, 1993, 12 (07) :773-784

[2] AMINES DERIVED FROM DIHALOPROPENES .2. SYNTHESIS OF (+/-)-1-(2-METHYLENE-1-AZIRIDINYL)-3-BUTEN-2-OL AND (-)-1-(2-METHYLENE-L-AZIRIDINYL))-3-BUTEN-2-OL [J].

BOTTINI, AT ;

DEV, V .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (03) :968-&

[3] HYDROBORATION OF TERPENES .9. A SIMPLE IMPROVED PROCEDURE FOR UPGRADING THE OPTICAL PURITY OF COMMERCIALLY AVAILABLE ALPHA-PINENES AND BETA-PINENES - CONVERSION OF (+)-ALPHA-PINENE TO (+)-BETA-PINENE VIA HYDROBORATION ISOMERIZATION [J].

BROWN, HC ;

JOSHI, NN .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4059-4062

[4] HYDROBORATION .82. ASYMMETRIC HYDROBORATION OF REPRESENTATIVE CIS DISUBSTITUTED AND HETEROCYCLIC OLEFINS WITH DICARANYLBORANES OF HIGH ENANTIOMERIC PURITY [J].

BROWN, HC ;

PRASAD, JVNV ;

ZAIDLEWICZ, M .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) :2911-2916

[5] VITAMIN-B12, A CATALYST IN THE SYNTHESIS OF PROSTAGLANDINS [J].

BUSATO, S ;

TINEMBART, O ;

ZHANG, ZD ;

SCHEFFOLD, R .

TETRAHEDRON, 1990, 46 (09) :3155-3166

[6] SYNTHESIS OF RETINALS WITH 8-MEMBERED AND 9-MEMBERED RINGS IN THE SIDE-CHAIN - MODELS FOR RHODOPSIN PHOTOBLEACHING INTERMEDIATES [J].

CALDWELL, CG ;

DERGUINI, F ;

BIGGE, CF ;

CHEN, AH ;

HU, SH ;

WANG, J ;

SASTRY, L ;

NAKANISHI, K .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (13) :3533-3537

[7] ENANTIOSELECTIVE EPOXIDATION OF CYCLIC 1,3-DIENES CATALYZED BY A STERICALLY AND ELECTRONICALLY OPTIMIZED (SALEN)MN COMPLEX [J].

CHANG, S ;

HEID, RM ;

JACOBSEN, EN .

TETRAHEDRON LETTERS, 1994, 35 (05) :669-672

[8] A SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].

CRANDALL, JK ;

BANKS, DB ;

COLYER, RA ;

WATKINS, RJ ;

ARRINGTO.JP .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) :423-&

[9]

CROWFORD RJ, 1976, CAN J CHEM, V54, P3364

[10] PALLADIUM-ASSISTED ROUTE TO CARBOCYCLIC NUCLEOSIDES - A FORMAL SYNTHESIS OF (+/-)-ARISTEROMYCIN [J].

DEARDORFF, DR ;

SHULMAN, MJ ;

SHEPPECK, JE .

TETRAHEDRON LETTERS, 1989, 30 (48) :6625-6628