High 1, 2-Asymmetric Induction in Radical Reactions: Radical Addition to. GAMMA.-Hydroxy. ALPHA.,. BETA.-Unsaturated Carboxylic Esters and Sulfones.

K Ogura, A Kayano, M Akazome

Index: Ogura, Katsuyuki; Kayano, Akio; Akazome, Motohiro Bulletin of the Chemical Society of Japan, 1997 , vol. 70, # 12 p. 3091 - 3101

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Citation Number: 11

Abstract

High 1, 2-asymmetric induction was realized by the addition of a 1-hydroxy-1-methylethyl radical to conformationally flexible (E)-γ-hydroxy α, β-unsaturated carboxylic esters and sulfones (1 and 2, respectively). Upon the irradiation (> 290 nm) of (E)-1 and benzophenone in 2-propanol, the 1-hydroxy-1-methylethyl radical was generated in situ and added to (E)-1 with high anti-stereoselectivity. The bulkier is the γ-alkyl group of (E)-1, the higher does ...