Premium
Asymmetric Conjugate Addition of Chiral Secondary Borylalkyl Copper Species
Author(s) -
Jang Won Jun,
Woo Jeongkyu,
Yun Jaesook
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202014425
Subject(s) - stereocenter , conjugate , enantioselective synthesis , reagent , chemistry , copper , combinatorial chemistry , yield (engineering) , catalysis , carbon fibers , organic chemistry , stereochemistry , materials science , mathematics , mathematical analysis , composite number , metallurgy , composite material
Abstract We report the diastereo‐ and enantioselective conjugate addition of chiral secondary borylalkyl copper species derived from borylalkenes in situ to α,β‐unsaturated diesters. In the presence of a chiral bisphosphine‐ligated CuH catalyst, the conjugate addition provides a direct access to enantioenriched alkylboron compounds containing two contiguous carbon stereogenic centers in good yield with high diastereo‐ and enantioselectivity (up to >98:2 dr, >99:1 er) by assembling readily available starting alkenyl reagents in a single operation without using preformed organometallic reagents or chiral auxiliaries. The resulting products were used in various organic transformations. The utility of the synthetic approach was highlighted by the synthesis of (−)‐phaseolinic acid.