Mediation of conformationally controlled photodecarboxylations of chiral and cyclic aryl esters by substrate structure, temperature, pressure, and medium constraints

T Mori, RG Weiss, Y Inoue

Index: Mori, Tadashi; Weiss, Richard G.; Inoue, Yoshihisa Journal of the American Chemical Society, 2004 , vol. 126, # 29 p. 8961 - 8975

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Citation Number: 41

Abstract

An aryl alkanoate, 2, 4, 6-trimethylphenyl (S)-(+)-2-methylbutyrate, whose ester group has a chiral center alpha to the carbonyl carbon and in which photo-Fries rearrangements are blocked by methyl substituents, undergoes facile photodecarboxylation under a variety of conditions and with complete retention of configuration. In fact, the decarboxylation process has many of the attributes of a symmetry-allowed suprafacial [1, 3] sigmatropic ...