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Synthesis 2009(13): 2289-2292  
DOI: 10.1055/s-0029-1216848
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Binaphthyl-Modified Quaternary Phosphonium Salts as Chiral Phase Transfer Catalysts: Application to Asymmetric Amination of β-Keto Esters

Rongjun He, Keiji Maruoka*
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
Fax: +81(75)7534041; e-Mail: maruoka@kuchem.kyoto-u.ac.jp;
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Publication History

Received 13 March 2009
Publication Date:
29 May 2009 (online)

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Abstract

A chiral quaternary tetraalkylphosphonium salt has been successfully utilized for the first time as a phase-transfer catalyst for asymmetric amination of β-keto esters in high yield with high ee. Asymmetric amination of a cyclic five-membered β-keto ester is a valuable method for preparing a key intermediate for asymmetric synthesis of aldose reductase inhibitor AS-3201 (Ranirestat).

Key words

amination - asymmetric synthesis - phase-transfer catalysis - phosphonium salts

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