Lewis acid mediated ring opening of propargylic epoxides: A stereospecific synthesis of 1,2-disubstituted homopropargylic alcohols

被引：21

作者：

Bernard, N ^{[1
]}

Chemla, F ^{[1
]}

Normant, JF ^{[1
]}

机构：

[1] Univ Paris 06, CNRS, Lab Chim Organoelements, F-75252 Paris 05, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 37期

关键词：

D O I：

10.1016/S0040-4039(98)01433-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thr BF3-Et2O-mediated ring opening of propargylic epoxides by organometallic nucleophiles gives in a completely regio- and stereospecific fashion 1,2-disubstituted homopropargylic alcohols in good to excellent yields. (C) 1998 Elsevier Science Lid. All rights reserved.

引用

页码：6715 / 6718

页数：4

共 22 条

[1] DIASTEREOSELECTIVE SYN OR ANTI OPENING OF PROPARGYLIC EPOXIDES - SYNTHESIS OF ALPHA-ALLENIC ALCOHOLS [J].

ALEXAKIS, A ;

MAREK, I ;

MANGENEY, P ;

NORMANT, JF .

TETRAHEDRON, 1991, 47 (09) :1677-1696

[2] STEREOCHEMICAL ASPECTS ON THE FORMATION OF CHIRAL ALLENES FROM PROPARGYLIC ETHERS AND EPOXIDES [J].

ALEXAKIS, A .

PURE AND APPLIED CHEMISTRY, 1992, 64 (03) :387-392

[3] Diastereoselective carbometalation of delta-mono and gamma-delta-bisubstituted Z vinyl metals [J].

Bahr, A ;

Marek, I ;

Normant, JF .

TETRAHEDRON LETTERS, 1996, 37 (33) :5873-5876

[4]

DEMONTELLANO PRO, 1973, J CHEM SOC CHEM COMM, P709

[5] SYNTHESIS AND OXIDIZING CYCLIZATION OF 2,3,5-TRIENE-1-OLS IN 5-HYDROXYALKYL-2-CYCLOPENTENE-1-ONES [J].

DOUTHEAU, A ;

SARTORETTI, J ;

GORE, J .

TETRAHEDRON, 1983, 39 (19) :3059-3065

[6] MECHANISM AND SYNTHETIC UTILITY OF BORON-TRIFLUORIDE ETHERATE PROMOTED ORGANO-LITHIUM ADDITIONS [J].

EIS, MJ ;

WROBEL, JE ;

GANEM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) :3693-3694

[7] General method for preparation of allenic zinc reagents by three-carbon homologation of triorganozincates: Convergent three-component coupling of propargylic substrates, triorganozincates, and electrophilic reagents [J].

Harada, T ;

Katsuhira, T ;

Osada, A ;

Iwazaki, K ;

Maejima, K ;

Oku, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (46) :11377-11390

[8]

HOFFMANN RW, 1993, LIEBIGS ANN CHEM, P629

[9]

KLEIJN H, 1982, RECL TRAV CHIM PAY B, V101, P97

[10] THE RING-OPENING OF UNSYMMETRICAL ALLYLIC, BENZYLIC, PROPARGYLIC, AND SI-SUBSTITUTED EPOXIDES BY TITANIUM ACETYLIDES - A CONVENIENT ACCESS TO CERTAIN 2-SUBSTITUTED 3-BUTYN-1-OLS [J].

KRAUSE, N ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (07) :1315-1320

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