Conjugate addition to 3-arylsulfinylchromones as a synthetic route to homochiral 2-substituted chromanones: scope and limitations

KJ Hodgetts, KI Maragkou, TW Wallace, RCR Wootton

Index: Hodgetts, Kevin J; Maragkou, Konstantina I; Wallace, Timothy W; Wootton, Robert C.R Tetrahedron, 2001 , vol. 57, # 31 p. 6793 - 6804

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Citation Number: 31

Abstract

A route to homochiral 2-substituted chromanones via the diastereoselective conjugate addition of organocopper reagents to 3-(p-tolylsulfinyl) chromones has been improved and used to prepare 2, 6-dimethylchromanone (S)-4 and LL-D253α methyl ether (S)-6. The attempted preparation of a 2-phenylchromanone (flavanone) using this strategy was unsuccessful due to the lability of the intermediate 2-phenyl-3-(p-tolylsulfinyl) chromanone ...