Volume 20, Issue 22
Preparative Organic Chemistry
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ChemInform Abstract: Asymmetric 1,4-Additions of Gilman Reagents to α,β-Disubstituted (E)-Enoylsultams/“Enolate” Protonations.

W, OPPOLZER

W, OPPOLZER

Dep. Chim. Org., Univ. Geneve. CH-1211 Geneve, Switz.

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A. J. KINGMA

A. J. KINGMA

Dep. Chim. Org., Univ. Geneve. CH-1211 Geneve, Switz.

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G. POLI

G. POLI

Dep. Chim. Org., Univ. Geneve. CH-1211 Geneve, Switz.

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First published: May 30, 1989

Abstract

Asymmetric addition of the organocopper reagents (II) to the N-enoyl sultams (I) yields the products (III) as sole diastereomers with purities of ≥ 98% after crystallization of the initially obtained diastereomeric mixtures of crude products.

ChemInform Abstract

Asymmetric addition of the organocopper reagents (II) to the N-enoyl sultams (I) yields the products (III) as sole diastereomers with purities of ≥ 98% after crystallization of the initially obtained diastereomeric mixtures of crude products. Hydrolysis of (III) affords the enantiomerically pure carboxylic acids (IV) containing two new stereogenic centers.

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