Beilstein J. Org. Chem.2013,9, 2224–2232, doi:10.3762/bjoc.9.261
product in moderate yields and up to 29% ee.
Keywords: asymmetric gold catalysis; chiral Au catalysts; gold-π interaction; NHCgoldcomplex; Introduction
After the long-held assumption of the non-reactivity of gold complexes, numerous reactions catalyzed by gold complexes have emerged in the last 2
. However, chiral gold complexes [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45], especially chiral NHC–goldcomplex-catalyzed asymmetric reactions [46][47][48][49][50][51][52][53] are still uncommon. Very few efficient chiral NHC–gold catalysts have been known up to the year of 2013. So
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Graphical Abstract
Figure 1:
Monodentate chiral NHC gold catalysts in recent years.
Beilstein J. Org. Chem.2011,7, 717–734, doi:10.3762/bjoc.7.82
dependent and did not operate in the presence of the NHC–goldcomplex [(IPr)AuOTf]. Thus, when cyclopropene 8 was treated with a stoichiometric quantity of EtOH in the presence of the latter catalyst (5 mol %), the tertiary allylic ether 9a was obtained with high regioselectivity (>99:1), but the yield (51
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Graphical Abstract
Scheme 1:
General reactivity of cyclopropenes in the presence of gold catalysts.