Straightforward Methodology for the Enantioselective Synthesis of Benzo[a]- and Indolo[2,3-a]quinolizidines 详细信息    查看全文 作者：Mercedes Amat ; Maria M. M. Santos ; Oriol Bassas ; Nú ; ria Llor ; Carmen Escolano ; Arantxa G&oacute ; mez-Esqué ; Elies Molins ; Steven M. Allin ; Vickie McKee ; Joan Bosch 刊名：Journal of Organic Chemistry 出版年：2007 出版时间：July 6, 2007 年：2007 卷：72 期：14 页码：5193 - 5201 全文大小：201K 年卷期：v.72,no.14(July 6, 2007) ISSN：1520-6904 文摘 LE>

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An enantioselective two-step route to substituted benzo[a]- and indolo[2,3-a]quinolizidines has beendeveloped. It consists of (i) a stereoselective cyclocondensation of a racemic or prochiral lta.gif" BORDER=0 >-oxo(di)esterwith either (S)-(3,4-dimethoxyphenyl)alaninol or (S)-tryptophanol in a process involving a dynamic kineticresolution and/or the differentiation of enantiotopic or diastereotopic ester groups, and (ii) a subsequentstereocontrolled cyclization on the aromatic ring taking advantage of the masked N-acyl iminium ionpresent in the resulting oxazolopiperidone lactams.