Organic letters

Synthesis of Optically Active 4-Substituted 2-Cyclohexenones

TI Houjeiry, SL Poe, DT McQuade

Index: Houjeiry, Tania I.; Poe, Sarah L.; McQuade, D. Tyler Organic Letters, 2012 , vol. 14, # 17 p. 4394 - 4397

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Citation Number: 20

Abstract

Recently, Nicolaou and Baran independently synthesized optically active 4-substituted 2- cyclohexenones via an efficient LiOH-mediated intramolecular aldol condensation. Thus far, application of their cyclization approach has been limited to ketoaldehydes where the R- group is branched. It is demonstrated that the LiOH-mediated cyclization, when applied to substrates containing unbranched R-groups, results in significant erosion of optical purity. ...