Open AccessSynthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration
Author(s) -
Rauful Alam,
Tobias Vollgraff,
Lars Eriksson,
Kálmán J. Szabó
Publication year - 2015
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.5b07498
Subject(s) - stereocenter , chemistry , catalysis , substrate (aquarium) , enantioselective synthesis , selectivity , combinatorial chemistry , stereochemistry , organic chemistry , oceanography , geology
Allylboration of ketones with γ-disubstituted allylboronic acids is performed in the presence of chiral BINOL derivatives. The reaction is suitable for single-step creation of adjacent quaternary stereocenters with high selectivity. We show that, with an appropriate choice of the chiral catalyst and the stereoisomeric prenyl substrate, full control of the stereo- and enantioselectivity is possible in the reaction.