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
ALEXAKIS, A
MAREK, I
MANGENEY, P
NORMANT, JF
[J]. TETRAHEDRON, 1991, 47 (09) : 1677 - 1696
[2] STEREOCHEMICAL ASPECTS ON THE FORMATION OF CHIRAL ALLENES FROM PROPARGYLIC ETHERS AND EPOXIDES
ALEXAKIS, A
[J]. PURE AND APPLIED CHEMISTRY, 1992, 64 (03) : 387 - 392
[3] Diastereoselective carbometalation of delta-mono and gamma-delta-bisubstituted Z vinyl metals
Bahr, A
Marek, I
Normant, JF
[J]. 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
DOUTHEAU, A
SARTORETTI, J
GORE, J
[J]. TETRAHEDRON, 1983, 39 (19) : 3059 - 3065
[6] MECHANISM AND SYNTHETIC UTILITY OF BORON-TRIFLUORIDE ETHERATE PROMOTED ORGANO-LITHIUM ADDITIONS
EIS, MJ
WROBEL, JE
GANEM, B
[J]. 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
Harada, T
Katsuhira, T
Osada, A
Iwazaki, K
Maejima, K
Oku, A
[J]. 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
KRAUSE, N
SEEBACH, D
[J]. CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (07): : 1315 - 1320

← 1 2 3 →