Studies on the Origin of 1, 5??anti Induction in Boron??Mediated Aldol Reactions

BL Stocker, P Teesdale??Spittle…

Index: Stocker, Bridget L.; Teesdale-Spittle, Paul; Hoberg, John O. European Journal of Organic Chemistry, 2004 , # 2 p. 330 - 336

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Citation Number: 25

Abstract

Abstract A model for the origin of selectivity in boron-mediated 1, 5-anti-aldols is presented. This model involves π-stacking between the boron enolate and a remote aromatic ring. A short, facile method for the synthesis of the C-12 to C-22 segment of peloruside A and its 1, 5- anti-aldol coupling using the proposed model is also presented.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)