Rhodium-catalyzed 1,4-addition of alkenylzirconocene chlorides to electron deficient alkenes

被引：25

作者：

Kakuuchi, A ^{[1
]}

Taguchi, T ^{[1
]}

Hanzawa, Y ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 06期

关键词：

D O I：

10.1016/j.tet.2003.08.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,4-conjugated addition of alkenylzirconocene chloride complexes to alpha,beta-enones, alpha,beta-enoic acid esters, and alpha,beta-enoic acid amides can be efficiently achieved by the use of [RhCl(cod)](2) catalyst. A high diastereoselectivity (95% yield, 90% de) was obtained through the reaction of alpha,beta-enoic acid amide derived from Oppolzer's sultam and 2-butenoyl chloride, while the use of Evans' chiral oxazolidinone as a chiral auxiliary in place of Oppolzer's sultam, gave a poor diastereoselectivity (98% yield, 26% de). (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1293 / 1299

页数：7

共 50 条

[21] Rhodium-Catalyzed Asymmetric 1,4-Addition of Heteroaryl Cyclic Triolborate to α,β-Unsaturated Carbonyl Compounds
Yu, Xiao-Qiang
Yamamoto, Yasunori
Miyaura, Norio
SYNLETT, 2009, (06) : 994 - 998
[22] Easily accessible chiral dicyclopentadiene ligands for rhodium-catalyzed enantioselective 1,4-addition reactions
Shao, Cheng
Yu, Hong-Jie
Feng, Chen-Guo
Wang, Rui
Lin, Guo-Qiang
TETRAHEDRON LETTERS, 2012, 53 (22) : 2733 - 2735
[23] Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactions
Duan, Wei-Liang
Iwamura, Hiroshi
Shintani, Ryo
Hayashi, Tamio
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) : 2130 - 2138
[24] Rhodium-catalyzed asymmetric 1,4-addition.
Hayashi, T
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : B195 - B195
[25] Rhodium-catalyzed coupling reaction of aroyl chlorides with alkenes
Sugihara, T
Satoh, T
Miura, M
Nomura, M
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1765 - 1772
[26] Rhodium-catalyzed asymmetric 1,4-addition of arylboron compounds generated in situ from aryl bromides
Takaya, Y
Ogasawara, M
Hayashi, T
TETRAHEDRON LETTERS, 1999, 40 (38) : 6957 - 6961
[27] Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine
Chen, G
Tokunaga, N
Hayashi, T
ORGANIC LETTERS, 2005, 7 (11) : 2285 - 2288
[28] Room-Temperature Rhodium-Catalyzed Asymmetric 1,4-Addition of Potassium Trifluoro(organo)borates
Gendrineau, Thomas
Genet, Jean-Pierre
Darses, Sylvain
ORGANIC LETTERS, 2009, 11 (15) : 3486 - 3489
[29] Chiral tetrafluorobenzobarrelenes as highly efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids
Nishimura, Takahiro
Nagaosa, Makoto
Hayashi, Tamio
CHEMISTRY LETTERS, 2008, 37 (08) : 860 - 861
[30] Rhodium-catalyzed asymmetric 1,4-addition of 3-thiopheneboronic acid to α,β-unsaturated carbonyl compounds
Yoshida, K
Hayashi, T
HETEROCYCLES, 2003, 59 (02) : 605 - 611

← 1 2 3 4 5 →