A convenient synthesis of (Z)-1-chloro-1-alkenes and (Z)-1-chloro-2-alkoxy-1-alkenes

被引：30

作者：

Baati, R

Barma, DK

Krishna, UM

Mioskowski, C ^{[1
]}

Falck, JR

机构：

[1] Univ Louis Pasteur Strasbourg 1, Fac Pharm, Lab Synth Bioorgan, UMR 7514, F-67401 Illkirch Graffenstaden, France

[2] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75390 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 06期

基金：

美国国家卫生研究院;

关键词：

alkenyl halides; carbenoids; chromium; enol ethers;

D O I：

10.1016/S0040-4039(01)02304-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mild, room temperature CrCl2 reduction of 1,1,1-trichloroalkanes stereoselectively generates (Z)-1-chloro-2-substituted-1-alkenes in excellent yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：959 / 961

页数：3

共 20 条

[1] AN EFFICIENT SYNTHESIS OF 1,3(E),5(Z), 1,3(E),5(E) AND 1,3(Z),5(Z)-TRIENES - APPLICATION TO THE SYNTHESIS OF GALBANOLENES AND (9Z,11E)-9,11,13-TETRADECATRIEN-1-YL ACETATE [J].

ALAMI, M ;

GUEUGNOT, S ;

DOMINGUES, E ;

LINSTRUMELLE, G .

TETRAHEDRON, 1995, 51 (04) :1209-1220

[2] Chromium vinylidene carbenoids: Generation, characterization, and reactivity. First evidence for an internal proton return phenomenon with vinylidene carbenoids [J].

Baati, R ;

Barma, DK ;

Falck, JR ;

Mioskowski, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9196-9197

[3] A convenient synthesis of 2-tetrahydrofuranyl ethers [J].

Baati, R ;

Valleix, A ;

Mioskowski, C ;

Barma, DK ;

Falck, JR .

ORGANIC LETTERS, 2000, 2 (04) :485-487

[4] VINYLIC ORGANOBORANES .12. SYNTHESIS OF (Z)-1-HALO-1-ALKENES VIA HYDROBORATION OF 1-HALO-1-ALKYNES FOLLOWED BY PROTONOLYSIS [J].

BROWN, HC ;

BLUE, CD ;

NELSON, DJ ;

BHAT, NG .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6064-6067

[5]

Concellón JM, 1999, ANGEW CHEM INT EDIT, V38, P2384, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2384::AID-ANIE2384>3.0.CO

[6]

2-3

[7] α-chlorovinylation:: Synthesis of 2-chloropropenyl and propargyl alcohols [J].

Falck, JR ;

Barma, DK ;

Mioskowski, C ;

Schlama, T .

TETRAHEDRON LETTERS, 1999, 40 (11) :2091-2094

[8]

Falck JR, 2001, ANGEW CHEM INT EDIT, V40, P1281, DOI 10.1002/1521-3773(20010401)40:7<1281::AID-ANIE1281>3.0.CO

[9]

2-B

[10]

GOSNEY I, 1995, COMPREHENSIVE ORGANI, V1, P719

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