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

Shuichi Oi; Takashi Sato; Yoshio Inoue

doi:10.1016/j.tetlet.2004.04.171

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

Shuichi Oi, Takashi Sato, Yoshio Inoue

Environment Conservation Center

Tohoku University

Research output: Contribution to journal › Article › peer-review

57 Citations (Scopus)

Abstract

Highly enantioselective 1,4-addition of alkenylzirconocene chlorides to α,β-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 up 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.

Original language	English
Pages (from-to)	5051-5055
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2004.04.171
Publication status	Published - 2004 Jun 21

Keywords

Alkenylzirconium
Asymmetric 1,4-addition
Rhodium catalyst
α,β-Enone

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10.1016/j.tetlet.2004.04.171

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abstract = "Highly enantioselective 1,4-addition of alkenylzirconocene chlorides to α,β-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 up 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.",

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author = "Shuichi Oi and Takashi Sato and Yoshio Inoue",

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T1 - Asymmetric 1,4-addition of alkenylzirconium reagents to α,β-unsaturated ketones catalyzed by chiral rhodium complexes

AU - Oi, Shuichi

AU - Sato, Takashi

AU - Inoue, Yoshio

PY - 2004/6/21

Y1 - 2004/6/21

N2 - Highly enantioselective 1,4-addition of alkenylzirconocene chlorides to α,β-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 up 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.

AB - Highly enantioselective 1,4-addition of alkenylzirconocene chlorides to α,β-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 up 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.

KW - Alkenylzirconium

KW - Asymmetric 1,4-addition

KW - Rhodium catalyst

KW - α,β-Enone

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DO - 10.1016/j.tetlet.2004.04.171

M3 - Article

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SN - 0040-4039

VL - 45

SP - 5051

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

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

Abstract

Keywords

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