A synthetic route to chiral C (3)-functionalized phthalides via a Ag (I)-catalyzed allylation/transesterification sequence

R Mirabdolbaghi, T Dudding

Index: Mirabdolbaghi, Roya; Dudding, Travis Tetrahedron, 2013 , vol. 69, # 15 p. 3287 - 3292

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Citation Number: 10

Abstract

A Ag (I)-catalyzed synthesis of chiral C (3)-substituted phthalides (8a–f) via a Sakurai– Hosomi allylation/transesterification reaction is described (ee≤ 86%). A notable feature of this reaction is that it utilizes ortho-substituted aldehydes, which are a class of compounds that generally afford poor levels of stereoinduction when applying most known catalytic asymmetric allylation approaches. It was also found that elongation of the n-alkyl chain ...