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Catalytic Asymmetric Conjugate Addition of a Borylalkyl Copper Complex for Chiral Organoboronate Synthesis.

Won Jun JangJaesook Yun
Published in: Angewandte Chemie (International ed. in English) (2019)
We report the catalytic enantioselective conjugate addition of a borylalkyl copper nucleophile generated in situ from a 1,1-diborylmethane derivative to α,β-unsaturated diesters. In the presence of a chiral N-heterocyclic carbene (NHC)-copper catalyst, this method facilitated the enantioselective incorporation of a CH2 Bpin moiety at the β-position of the diesters to yield β-chiral alkyl boronates in up to 86 % yield with high enantioselectivity. The alkylboron moiety in the resulting chiral diester products was converted into various functional groups by organic transformation of the C-B bond.
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