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Catalytic Asymmetric Conjugate Addition of a Borylalkyl Copper Complex for Chiral Organoboronate Synthesis
Author(s) -
Jang Won Jun,
Yun Jaesook
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201909712
Subject(s) - enantioselective synthesis , moiety , conjugate , chemistry , carbene , nucleophile , catalysis , yield (engineering) , copper , alkyl , stereochemistry , derivative (finance) , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , mathematical analysis , mathematics , economics , financial economics , metallurgy
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 CH 2 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.