Asymmetric 1,4-addition of alkenylzirconium reagents to α,β-unsaturated ketones catalyzed by chiral rhodium complexes

被引：47

作者：

Oi, S ^{[1
]}

Sato, T ^{[1
]}

Inoue, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Engn, Dept Biomol Engn, Sendai, Miyagi 9808579, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 26期

关键词：

asymmetric 1,4-addition; alkenylzirconium; rhodium catalyst; alpha; beta-enone;

D O I：

10.1016/j.tetlet.2004.04.171

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantioselective 1,4-addition of alkenylzirconocene chlorides to alpha-enones Was found to be catalyzed by a chiral rhodium complex generated from [Rh(cod)(MeCN)(2)]BF4 and (S)-BINAP. The reaction can be applied to either cyclic or acyclic enones and the optical yield was LIP to 99% ee. The reaction mechanism would involve the transmetalation between the alkenylzirconocene chloride and the rhodium complex to give the alkenylrhodium species as a key intermediate. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5051 / 5055

页数：5

共 50 条

[1] Rhodium-catalyzed asymmetric 1,4-addition of arylboron reagents to α,β-unsaturated esters
Takaya, Y
Senda, T
Kurushima, H
Ogasawara, M
Hayashi, T
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (20) : 4047 - 4056
[2] Mechanistic studies on the catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of aryltitanate reagents to α,β-unsaturated ketones
Tokunaga, N
Yoshida, K
Hayashi, T
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5445 - 5449
[3] Chiral Tetrafluorobenzobarrelenes as Effective Ligands for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboroxines to β,β-Disubstituted α,β-Unsaturated Ketones
Shintani, Ryo
Takeda, Momotaro
Nishimura, Takahiro
Hayashi, Tamio
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (23) : 3969 - 3971
[4] Rhodium-catalyzed asymmetric 1,4-addition of organometallic reagents
T. Hayashi
[J]. Russian Chemical Bulletin, 2003, 52 : 2595 - 2605
[5] Rhodium-catalyzed asymmetric 1,4-addition of organometallic reagents
Hayashi, T
[J]. RUSSIAN CHEMICAL BULLETIN, 2003, 52 (12) : 2595 - 2605
[6] Asymmetric 1,4-addition of organosiloxanes to α,β-unsaturated carbonyl compounds catalyzed by a chiral rhodium complex
Oi, S
Taira, A
Honma, Y
Inoue, Y
[J]. ORGANIC LETTERS, 2003, 5 (01) : 97 - 99
[7] Asymmetric 1,4-addition of aryltrialkoxysilanes to α,β-unsaturated esters and amides catalyzed by a chiral rhodium complex
Oi, S
Taira, A
Honma, Y
Sato, T
Inoue, Y
[J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 598 - 602
[8] High performance of a chiral diene-rhodium catalyst for the asymmetric 1,4-addition of arylboroxines to α,β-unsaturated ketones
Chen, FX
Kina, A
Hayashi, T
[J]. ORGANIC LETTERS, 2006, 8 (02) : 341 - 344
[9] Asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated aldehydes catalyzed by a chiral diene-rhodium complex
Hayashi, T
Tokunaga, N
Okamoto, K
Shintani, R
[J]. CHEMISTRY LETTERS, 2005, 34 (11) : 1480 - 1481
[10] Rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated amides
Sakuma, S
Miyaura, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26): : 8944 - 8946

← 1 2 3 4 5 →