A Sterically-Encumbered, C 2-Symmetric Chiral Acetal for Enhanced Asymmetric Induction in the Pauson-Khand Reaction

…, AS Felts, C Hirosawa, S Kerrigan

Index: Krafft, Marie E.; Bonaga, Llorente V. R.; Felts, Andrew S.; Hirosawa, Chitaru; Kerrigan, Sean Journal of Organic Chemistry, 2003 , vol. 68, # 15 p. 6039 - 6042

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Citation Number: 24

Abstract

Meanwhile, de Meijere and co-workers reported the construction of an enantiopure spiro(cyclopropane-1,4'-bicyclo[3.3.0]oct-1-en-3-one), 4, derived from a diastereoselective PKR of a 1,6-cyclopropylidenyne bearing a propargylic C 2 -symmetric chiral acetal (Scheme 1). 19,20 It was conceived that a larger alkyl group (R = C(CH 3 ) 2 OCH 3 ) 21 in a tartrate-derived chiral auxiliary, as in diol 5, should improve the diastereoselectivity of the cycloaddition. ...