Journal of Organic Chemistry 2005-04-29

Simple diastereoselectivity of the BF3.OEt2-catalyzed vinylogous Mukaiyama aldol reaction of 2-(trimethylsiloxy)furans with aldehydes.

Carlos Silva López, Rosana Alvarez, Belén Vaz, Olalla Nieto Faza, Angel R de Lera

Index: J. Org. Chem. 70(9) , 3654-9, (2005)

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Abstract

[reaction: see text] A comprehensive scan of the transition state space for the reaction of 2-(trimethylsiloxy)furan and methacrolein (24 combinations) offered a satisfactory explanation of the high like diastereoselectivity obtained experimentally in the Mukaiyama vinylogous aldol reaction of these and related partners. It was determined that the syn-gamma-hydroxyalkylbutenolides are formed preferentially following a g(+) orientation of the two reactants with the aldehyde in the s-trans conformation. Diastereoselectivity is shown to be caused by a combination of subtle effects favoring the formation of the like product.