Tetrahedron

Effect of A (1, 3)-cis strain on the asymmetric epoxidation of (E)-and (Z)-6, 6-diethoxy-3-hexen-2-ols and 4-methyl-6, 6-diethoxy-3-hexen-2-ols

…, IG Taran, IE Mikerin, VI Shvets, YE Raifeld, SA Lang…

Index: Nikitenko, Antonia A.; Arshava, Boris M.; Taran, Irina G.; Mikerin, Igor E.; Shvets, Vitaly I.; Raifeld, Yuri E.; Lang Jr., Stanley A.; Lee, Ving J. Tetrahedron, 1998 , vol. 54, # 39 p. 11731 - 11740

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Citation Number: 3

Abstract

The effect of A (1, 3)-cis strain on the diastereoselectivity of epoxidation of (E)-and (Z)-6, 6- diethoxy-3-hexen-2-ols and 4-methyl-6, 6-diethoxy-3-hexen-2-ols is analyzed, with some empiric observations provided. Increased A (1, 3)-cis strain results in increased amounts of racemic threo-epoxy alcohols, while high ee's are found for the erythro-epoxy alcohols.