Zirconium-catalyzed asymmetric carboalumination (ZACA reaction) of 1,4-dienes

被引：18

作者：

Tan, Z ^{[1
]}

Liang, B ^{[1
]}

Huo, SQ ^{[1
]}

Shi, JC ^{[1
]}

Negishi, E ^{[1
]}

机构：

[1] Purdue Univ, Herbert C Brown Lab Chem, W Lafayette, IN 47907 USA

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 04期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/j.tetasy.2006.01.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Variously substituted 1,4-dienes containing a terminal vinyl (H2C=CH) group, readily undergo the ZACA reaction with Me3Al and higher alkylalanes in a 1: 1 molar ratio in the presence of a catalytic amount (1-5 mol %) of bis[(1-neomenthyl)indenyl]zirconium dichloride in good yields and in good enantioselectivity (70-92% ee), thereby providing an efficient and convenient route to various alkene-containing chiral natural products. Only the reaction of the parent 1,4-pentadiene is accompanied by extensive racemization. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：512 / 515

页数：4

共 50 条

[41] A NOVEL TYPE OF ZIRCONIUM-CATALYZED OR ZIRCONIUM-PROMOTED CYCLIZATION REACTION
TAKAHASHI, T
KONDAKOV, DY
SUZUKI, N
ORGANOMETALLICS, 1994, 13 (09) : 3411 - 3412
[42] PD-II-CATALYZED ISOMERIZATIONS OF 3-ACETOXY-1,4-DIENES TO 1-ACETOXY-2,4-DIENES - STEREOCHEMICAL AND PREPARATIVE ASPECTS
GOLDING, BT
PIERPOINT, C
ANEJA, R
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (20) : 1030 - 1031
[43] Synthesis of heterocycles using zirconium-catalyzed asymmetric diene cyclization
Yamaura, Y
Hyakutake, M
Mori, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (32) : 7615 - 7616
[44] SYNTHESES WITH SULFONES .48. STEREOSELECTIVE SYNTHESIS OF 2-ISOPROPYL- 1,4-DIENES THROUGH THE IRON-CATALYZED CROSS-COUPLING REACTION OF 2-BENZENESULFONYL- 1,4-DIENES AND ISOPROPYLMAGNESIUM CHLORIDE
ALVAREZ, E
CUVIGNY, T
DUPENHOAT, CH
JULIA, M
TETRAHEDRON, 1988, 44 (01) : 111 - 118
[45] Highly efficient asymmetric synthesis of fluvirucinine A1, via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)-lipase-catalyzed acetylation tandem process
Liang, Bo
Negishi, Ekichi
ORGANIC LETTERS, 2008, 10 (02) : 193 - 195
[46] Synthesis of heterocycles using zirconium-catalyzed asymmetric diene cyclization
J Am Chem Soc, 32 (7615):
[47] STEREOSPECIFIC SYNTHESIS OF 1,4-DIENES .2.
HATA, G
AOKI, D
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (12): : 3754 - &
[48] Auxiliary-directed peroxidation of 1,4-dienes
Tetrahedron, 38 (12381):
[49] Regio- and stereoselective synthesis of 1,4-dienes
Oishi, Shigeki
Hatano, Keisuke
Tsubouchi, Akira
Takeda, Takeshi
CHEMICAL COMMUNICATIONS, 2011, 47 (42) : 11639 - 11640
[50] AUXILIARY-DIRECTED PEROXIDATION OF 1,4-DIENES
DUSSAULT, PH
HAYDEN, MR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 46 - ORGN

← 1 2 3 4 5 →