Volume 31, Issue 23
Heterocyclic Compounds
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ChemInform Abstract: Synthesis of Optically Active 5-Substituted-2-pyrrolidinone Derivatives Having Atropisomeric Structure and 3,5-cis-Selective Reaction of Their Enolates with Electrophiles.

Masao Fujita

Masao Fujita

Tokyo Univ. Pharm. Life Sci., Hachioji, Tokyo 192-03, Japan

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Osamu Kitagawa

Osamu Kitagawa

Tokyo Univ. Pharm. Life Sci., Hachioji, Tokyo 192-03, Japan

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Yoichiro Yamada

Yoichiro Yamada

Tokyo Univ. Pharm. Life Sci., Hachioji, Tokyo 192-03, Japan

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Hirotaka Izawa

Hirotaka Izawa

Tokyo Univ. Pharm. Life Sci., Hachioji, Tokyo 192-03, Japan

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Hiroshi Hasegawa

Hiroshi Hasegawa

Tokyo Univ. Pharm. Life Sci., Hachioji, Tokyo 192-03, Japan

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Takeo Taguchi

Takeo Taguchi

Tokyo Univ. Pharm. Life Sci., Hachioji, Tokyo 192-03, Japan

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First published: 08 June 2010

Abstract

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ChemInform Abstract

Starting from the butyrolactone (I) the pyrrolidinone (IV) having atropisomerism and the derivative (IX) having an atropisomerism-like structure can be prepared in optically pure form. The reaction of their Li-enolates with electrophiles allows stereoselective formation of 3,5-cis-substituted products, which is unusual.

chemical structure image

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