Direct catalytic asymmetric aldol-Tishchenko reaction.

Direct catalytic asymmetric aldol-Tishchenko reaction. Research Abstract Details 

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Direct catalytic asymmetric aldol-Tishchenko reaction. Abstract Text:

Vijay Gnanadesikan,Yoshihiro Horiuchi,Takashi Ohshima,Masakatsu Shibasaki,

A direct catalytic asymmetric aldol reaction of propionate equivalent was achieved via the aldol-Tishchenko reaction. Coupling an irreversible Tishchenko reaction to a reversible aldol reaction overcame the retro-aldol reaction problem and thereby afforded the products in high enantio and diastereoselectivity using 10 mol % of the asymmetric catalyst. A variety of ketones and aldehydes, including propyl and butyl ketones, were coupled efficiently, yielding the corresponding aldol-Tishchenko products in up to 96% yield and 95% ee. Diastereoselectivity was generally below the detection limit of 1H NMR (>98:2). Preliminary studies performed to clarify the mechanism revealed that the aldol products were racemic with no diastereoselectivity. On the other hand, the Tishchenko products were obtained in a highly enantiocontrolled manner.

Direct catalytic asymmetric aldol-Tishchenko reaction. Publishing Authors By Initials

V Gnanadesikan,Y Horiuchi,T Ohshima,M Shibasaki,

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Direct catalytic asymmetric aldol-Tishchenko reaction. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of the American Chemical Society

VOLUME: 126

Page Numbers: 7782-3

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 30

MONTH: Jun

YEAR: 2004

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LANGUAGE: eng

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Grant and Affiliation Information for Direct catalytic asymmetric aldol-Tishchenko reaction.

AFFILIATION: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.

Country: United States

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MEDLINETA: J Am Chem Soc

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