Stereoselective synthesis of Z alkenyl halides via Julia olefination

被引：55

作者：

Lebrun, ME ^{[1
]}

Le Marquand, P ^{[1
]}

Berthelette, C ^{[1
]}

机构：

[1] Merck Frosst Ctr Therapeut Res, Dept Med Chem, Pointe Claire, PQ H9R 4P8, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 05期

关键词：

D O I：

10.1021/jo052370h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Julia olefination between alpha-halomethyl sulfones and a variety of aldehydes afforded alkenyl halides in good to excellent yields with high E/Z stereo selectivities. Sulfones were readily prepared in two or three steps from commercially available reagents in good yields. Optimization revealed that the nature of the Z solvent, the base, and the additive were crucial to obtain the desired alkenyl halides.

引用

页码：2009 / 2013

页数：5

共 33 条

[1] A convenient synthesis of (Z)-1-chloro-1-alkenes and (Z)-1-chloro-2-alkoxy-1-alkenes
Baati, R
Barma, DK
Krishna, UM
Mioskowski, C
Falck, JR
[J]. TETRAHEDRON LETTERS, 2002, 43 (06) : 959 - 961
[2] A versatile synthesis of 2-haloalk-2(Z)-en-1-ols and 1-chloro-1(Z)-alkenes from trichloromethylcarbinols
Baati, R
Barma, DK
Falck, JR
Mioskowski, C
[J]. TETRAHEDRON LETTERS, 2002, 43 (12) : 2183 - 2185
[3] Highly stereoselective synthesis of conjugated polyenes via a homocoupling reaction of unsaturated silanes
Babudri, F
Cicciomessere, AR
Farinola, GM
Fiandanese, V
Marchese, G
Musio, R
Naso, F
Sciacovelli, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) : 3291 - 3298
[4] A DIRECT SYNTHESIS OF OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH LITHIO DERIVATIVES OF 2-[ALKYL-SULFONYL OR (2'-ALKENYL)-SULFONYL OR BENZYL-SULFONYL]-BENZOTHIAZOLES
BAUDIN, JB
HAREAU, G
JULIA, SA
RUEL, O
[J]. TETRAHEDRON LETTERS, 1991, 32 (09) : 1175 - 1178
[5] BAUDIN JB, 1993, B SOC CHIM FR, V130, P336
[6] BAUDIN JB, 1993, B SOC CHIM FR, V130, P856
[7] Bellingham R, 1996, SYNTHESIS-STUTTGART, P285
[8] The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds
Blakemore, PR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23): : 2563 - 2585
[9] Blakemore PR, 1998, SYNLETT, P26
[10] An expedient approach to E,Z-dienes using the Julia olefination (vol 42, pg 5149, 2001)
Charette, AB
Berthelette, C
St-Martin, D
[J]. TETRAHEDRON LETTERS, 2001, 42 (37) : 6619 - 6619

← 1 2 3 4 →