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Stereocontrolled Synthesis of 1,5‐Stereogenic Centers through Three‐Carbon Homologation of Boronic Esters
Author(s) -
Unsworth Phillip J.,
Leonori Daniele,
Aggarwal Varinder K.
Publication year - 2014
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.201405700
Subject(s) - stereocenter , pinacol , borylation , allylic rearrangement , chemistry , isomerization , stereoselectivity , stereochemistry , boronic acid , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , aryl , alkyl
Allylic pinacol boronic esters are stable toward 1,3‐borotropic rearrangement. We developed a Pd II ‐mediated isomerization process that gives di‐ or trisubstituted allylic boronic esters with high E selectivity. The combination of this method with lithiation–borylation enables the synthesis of carbon chains that bear 1,5‐stereogenic centers. The utility of this method has been demonstrated in a formal synthesis of (+)‐jasplakinolide.
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