TY - JOUR
T1 - Organocatalytic transfer hydrogenation of cyclic enones
AU - Tuttle, Jamison B.
AU - Ouellet, Stéphane G.
AU - MacMillan, David W.C.
N1 - Copyright:
Copyright 2010 Elsevier B.V., All rights reserved.
PY - 2006/10/4
Y1 - 2006/10/4
N2 - The first enantioselective organocatalytic transfer hydrogenation of cyclic enones has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of β,β-substituted α,β-unsaturated cycloalkenones, to generate β-stereogenic cyclic ketones. The use of imidazolidinone 4 as the asymmetric catalyst has been found to mediate the hydrogenation of a large class of enone substrates with tert-butyl Hantzsch ester serving as an inexpensive source of hydrogen. The capacity of catalyst 4 to enable enantioselective transfer hydrogenation of cycloalkenones has been extended to five-, six-, and seven-membered ring systems. The sense of asymmetric induction is in complete accord with the stereochemical model first reported in conjunction with the use of catalyst 4 for enantioselective ketone Diels-Alder reactions.
AB - The first enantioselective organocatalytic transfer hydrogenation of cyclic enones has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of β,β-substituted α,β-unsaturated cycloalkenones, to generate β-stereogenic cyclic ketones. The use of imidazolidinone 4 as the asymmetric catalyst has been found to mediate the hydrogenation of a large class of enone substrates with tert-butyl Hantzsch ester serving as an inexpensive source of hydrogen. The capacity of catalyst 4 to enable enantioselective transfer hydrogenation of cycloalkenones has been extended to five-, six-, and seven-membered ring systems. The sense of asymmetric induction is in complete accord with the stereochemical model first reported in conjunction with the use of catalyst 4 for enantioselective ketone Diels-Alder reactions.
UR - http://www.scopus.com/inward/record.url?scp=33749516633&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33749516633&partnerID=8YFLogxK
U2 - 10.1021/ja0653066
DO - 10.1021/ja0653066
M3 - Article
C2 - 17002356
AN - SCOPUS:33749516633
VL - 128
SP - 12662
EP - 12663
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 39
ER -