Straightforward Methodology for the Enantioselective Synthesis of Benzo[a]- and Indolo[2,3-a]quinolizidines
The Journal of Organic Chemistry2007Vol. 72(14), pp. 5193–5201
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Mercedes Amat, Maria M. M. Santos, O. Bassas, Núria Llor, Carmen Escolano, A. Gomez-Esque, Elı́es Molins, Steven M. Allin, Vickie McKee, Joan Bosch
Abstract
An enantioselective two-step route to substituted benzo[a]- and indolo[2,3-a]quinolizidines has been developed. It consists of (i) a stereoselective cyclocondensation of a racemic or prochiral delta-oxo(di)ester with either (S)-(3,4-dimethoxyphenyl)alaninol or (S)-tryptophanol in a process involving a dynamic kinetic resolution and/or the differentiation of enantiotopic or diastereotopic ester groups, and (ii) a subsequent stereocontrolled cyclization on the aromatic ring taking advantage of the masked N-acyl iminium ion present in the resulting oxazolopiperidone lactams.
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