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Enantioselective Synthesis and Cross‐Coupling of Tertiary Propargylic Boronic Esters Using Lithiation–Borylation of Propargylic Carbamates
Author(s) -
Partridge Benjamin M.,
ChaussetBoissarie Laëtitia,
Burns Matthew,
Pulis Alexander P.,
Aggarwal Varinder K.
Publication year - 2012
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.201203198
Subject(s) - borylation , chemistry , enantioselective synthesis , stereoselectivity , boronic acid , organic chemistry , combinatorial chemistry , catalysis , aryl , alkyl
Lithiation–borylation of propargylic carbamates leads to tertiary propargylic boronic esters in very high e.r., provided that ethylene glycol boronic esters are used. These versatile intermediates undergo a range of highly stereoselective transformations, including protodeboronation to give tertiary allenes and Suzuki–Miyaura cross‐couplings of tertiary boron species leading to tetrasubstituted allenes with high enantiospecificity.