doi: 10.1021/jacs.5b07498.
Epub 2015 Aug 31.
Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration
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- PMID: 26316158
- DOI: 10.1021/jacs.5b07498
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Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration
J Am Chem Soc.
.
Free article
Abstract
Allylboration of ketones with γ-disubstituted allylboronic acids is performed in the presence of chiral BINOL derivatives. The reaction is suitable for single-step creation of adjacent quaternary stereocenters with high selectivity. We show that, with an appropriate choice of the chiral catalyst and the stereoisomeric prenyl substrate, full control of the stereo- and enantioselectivity is possible in the reaction.
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