1, 2-Asymmetric induction in reactions of nonconjugated acyclic radicals: a new model for highly selective atom-transfer reactions of alkyl-substituted radicals

…, SV Geib, B Giese, W Damm, F Wetterich

Index: Thoma, Gebhard; Curran, Dennis P.; Geib, Steven V.; Giese, Bernd; Damm, Wolfgang; Wetterich, Frank Journal of the American Chemical Society, 1993 , vol. 115, # 19 p. 8585 - 8591

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Citation Number: 25

Abstract

Abstract: The iodine-transfer addition of methyliodomalonodinitrile (1) to several dialkyl- substituted olefins is reported. The iodine-transfer reaction to the acyclic nonconjugated radical intermediates often results in selective product formation due to 1, 2-asymmetric induction. The level of diastereoselectivity depends on the size of the alkyl substituent on the radical. Tertiary alkyl groups give high syn selectivity, secondary groups lead to a ...