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Catalytic Asymmetric Synthesis of Phosphine Boronates
Author(s) -
Hornillos Valentín,
Vila Carlos,
Otten Edwin,
Feringa Ben L.
Publication year - 2015
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.201502987
Subject(s) - phosphine , enantioselective synthesis , stereospecificity , vicinal , phosphine oxide , chemistry , optically active , enantiomer , catalysis , enantiomeric excess , organic chemistry , combinatorial chemistry , copper
The first catalytic enantioselective synthesis of ambiphilic phosphine boronate esters is presented. The asymmetric boration of α,β‐unsaturated phosphine oxides catalyzed by a copper bisphosphine complex affords optically active organoboronate esters that bear a vicinal phosphine oxide group in good yields and high enantiomeric excess. The synthetic utility of the products is demonstrated through stereospecific transformations into multifunctional optically active compounds.