Development of New Asymmetric Reactions Utilizing Tartaric Acid Esters as Chiral Auxiliaries. The Design of an Efficient Chiral Multinucleating System

Yutaka Ukaji; Katsuhiko Inomata

doi:10.1055/s-2003-39879

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Synlett 2003(8): 1075-1087
DOI: 10.1055/s-2003-39879

ACCOUNT

Development of New Asymmetric Reactions Utilizing Tartaric Acid Esters as Chiral Auxiliaries. The Design of an Efficient Chiral Multinucleating System

Yutaka Ukaji, Katsuhiko Inomata*
Department of Chemical Science, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
Fax: +81(76)2645742; e-Mail: inomata@cacheibm.s.kanazawa-u.ac.jp;

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Publication History

Received 7 May 2003
Publication Date:
11 June 2003 (online)

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Abstract

A practical method for the construction of chiral molecules has been designed using a novel strategy based on systems possessing multiple metal centers and tartaric acid esters as chiral auxiliaries. By using this design, we have developed methods for carrying out highly enantioselective (1) Simmons-Smith reaction, (2) 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrones, and (3) nucleophilic additions of organometallic compounds to imine derivatives.

Key words

asymmetric synthesis - tartaric acid esters - Simmons-Smith reaction - 1,3-dipolar cycloadditions - nucleophilic additions to imine derivatives

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