HIGHLY REGIOSELECTIVE, (E)-STEREOSELECTIVE AND DIASTEREOSELECTIVE SN2' ADDITION OF ORGANOCUPRATES TO CHIRAL ALLYLIC CYCLIC CARBONATES

被引：25

作者：

KANG, SK

LEE, DH

SIM, HS

LIM, JS

机构：

[1] Department of Chemistry, Sung Kyun Kwan University, Suwon, 440-746, Natural Science Campus

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(00)60065-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the cyclic carbonates of acyclic vinyl diols with RCu(CN)Li.BF3, RCu(CN)MgBr-BF3, or RMgBr.CuI (cat) in THF at -78-degrees-C proceeded in S(N)2' fashion and resulted in the formation of alkylated (E)-allylic alcohols with remarkably high diastereoselectivity. This reaction represents an efficient 1, 3-chirality transfer method.

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页码：91 / 94

页数：4

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共 26 条

[1] COPPER-CATALYZED REACTIONS OF ORGANOTITANIUM REAGENTS - HIGHLY SN2' SELECTIVE AND ANTI-SELECTIVE AND DIASTEREOSELECTIVE AND CHEMOSELECTIVE ALKYLATION OF ALLYLIC CHLORIDES AND PHOSPHATES [J].

ARAI, M ;

NAKAMURA, E ;

LIPSHUTZ, BH .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5489-5493

[2] 1,4-BISMETHANESULFONATES OF STEREOISOMERIC BUTANETETRAOLS + RELATED COMPOUNDS [J].

FEIT, PW .

JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (01) :14-+

[3] ALKYLATION OF ALLYLIC DERIVATIVES .5. LOSS OF DOUBLE-BOND CONFIGURATION ASSOCIATED WITH ALPHA-ALKYLATION OF ALLYLIC CARBOXYLATES WITH DIALKYLCUPRATES [J].

GOERING, HL ;

KANTNER, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (05) :721-724

[4] STEREOCHEMISTRY OF CONVERSION OF ALLYLIC ESTERS TO OLEFINS WITH LITHIUM DIALKYLCUPRATES [J].

GOERING, HL ;

SINGLETON, VD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) :7854-7855

[5] ALKYLATION OF ALLYLIC DERIVATIVES .8. REGIOCHEMISTRY AND STEREOCHEMISTRY OF ALKYLATION OF ALLYLIC CARBOXYLATES WITH LITHIUM METHYLCYANOCUPRATE [J].

GOERING, HL ;

KANTNER, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :422-426

[6] ALKYLATION OF ALLYLIC DERIVATIVES .6. REGIOCHEMISTRY OF ALKYLATION OF ALLYLIC ACETATES WITH DIALKYLCUPRATES [J].

GOERING, HL ;

SINGLETON, VD .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (09) :1531-1533

[7] ALKYLATION OF ALLYLIC DERIVATIVES .7. STEREOCHEMISTRY OF ALKYLATION OF THE ISOMERIC TRANS-ALPHA,GAMMA-METHYL(PHENYL)ALLYL ACETATES WITH LITHIUM DIALKYLCUPRATES AND ALKYLCYANOCUPRATES [J].

GOERING, HL ;

TSENG, CC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :3986-3990

[8] A HIGHLY STEREOSELECTIVE SYNTHESIS OF (E)-ALKENE DIPEPTIDE ISOSTERES VIA ORGANOCYANOCOPPER - LEWIS ACID MEDIATED REACTION [J].

IBUKA, T ;

HABASHITA, H ;

OTAKA, A ;

FUJII, N ;

OGUCHI, Y ;

UYEHARA, T ;

YAMAMOTO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4370-4382

[9] A REGIO-SELECTIVE, (E)-STEREO-SELECTIVE, AND CHEMO-SELECTIVE SYNTHESIS OF UNSYMMETRICAL DIVINYLMETHANOLS STARTING FROM L-TARTRATE AND D-TARTRATE VIA ORGANOCYANOCOPPER LEWIS ACID MEDIATED 1,3-CHIRALITY TRANSFER [J].

IBUKA, T ;

TANAKA, M ;

YAMAMOTO, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) :967-969

[10] AN EFFICIENT SYNTHESIS OF CHIRAL QUATERNARY CARBON CENTERS WITH HIGH OPTICAL PURITY VIA 1,3-CHIRALITY TRANSFER [J].

IBUKA, T ;

TANAKA, M ;

NISHII, S ;

YAMAMOTO, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (20) :1596-1598