Catalytic Enantioselective Pyrrole Alkylations of α,β-Unsaturated 2-Acyl Imidazoles
Organic Letters2006Vol. 8(11), pp. 2249–2252
Citations Over TimeTop 10% of 2006 papers
Abstract
[reaction: see text] Enantioselective additions of pyrroles to alpha,beta-unsaturated 2-acyl imidazoles catalyzed by the bis(oxazolinyl)pyridine-scandium(III) triflate complex (1) have been accomplished. The alpha,beta-unsaturated 2-acyl imidazoles were synthesized in high yields through Wittig olefination. A short, enantioselective synthesis of the alkaloid (+)-heliotridane has been accomplished utilizing this methodology and a 2-acyl imidazole cleavage and cyclization. This methodology was then extended to the one-pot asymmetric synthesis of 2-substituted indoles.
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