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Catalytic Asymmetric Epoxidation of Alpha,beta-Unsaturated Esters With Chiral Yttrium-Biaryldiol Complexes

Catalytic Asymmetric Epoxidation of Alpha,beta-Unsaturated Esters With Chiral Yttrium-Biaryldiol Complexes

Hiroyuki Kakei, Riichiro Tsuji, Takashi Ohshima, Hiroyuki Morimoto, Shigeki Matsunaga, Masakatsu Shibasaki

Chem Asian J. 2007 Feb 5;2(2):257-64.

PMID: 17441160

Abstract:

The full details of the asymmetric epoxidation of alpha,beta-unsaturated esters catalyzed by yttrium complexes with biaryldiol ligands are described. An yttrium-biphenyldiol catalyst, generated from Y(OiPr)3-biphenyldiol ligand-triphenylarsine oxide (1:1:1), is suitable for the epoxidation of various alpha,beta-unsaturated esters. With this catalyst, beta-aryl alpha,beta-unsaturated esters gave high enantioselectivities and good yields (< or = 99% ee). The reactivity of this catalyst is good, and the catalyst loading could be decreased to as little as 0.5-2 mol % (the turnover number was up to 116), while high enantiomeric excesses were maintained. For beta-alkyl alpha,beta-unsaturated esters, an yttrium-binol catalyst, generated from Y(OiPr)3-binol ligand-triphenylphosphine oxide (1:1:2), gave the best enantioselectivities (< or = 97% ee). The utility of the epoxidation reaction was demonstrated in an efficient synthesis of (-)-ragaglitazar, a potential antidiabetes agent.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1153055	Triphenylarsine oxide		1153-05-5	Price

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