Enantioselective Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters: Methodology and Applications

Authors


  • We thank the EPSRC and the European Research Council (ERC) in the context of the European Community′s Seventh Framework Programme (FP7/2007-2013, ERC grant no. 246785) for financial support. V.K.A. thanks the Royal Society for a Wolfson Research Merit Award and EPSRC for a Senior Research Fellowship. R. L-G. is grateful to the FQRNT for a postdoctoral fellowship. We thank Frontier Scientific for generous donation of boronic acids and boronic esters.

Abstract

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Pin it down: A range of substrates that bear versatile functional groups with quaternary stereogenic centers have been prepared with very high enantioselectivity from tertiary boronic esters (see scheme; Cb=N,N-diisopropylcarbamoyl, pin=pinacolato). The preparation of allylboronic esters bearing contiguous quaternary and tertiary stereogenic centers, and applications to natural product synthesis are also reported.

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