Straightforward methodology for the enantioselective synthesis of benzo[a]- and indolo[2,3-a]quinolizidines

被引：58

作者：

Amat, Mercedes ^{[1
]}

Santos, Maria M. M.

Bassas, Oriol

Llor, Nuria

Escolano, Carmen

Gomez-Esque, Arantxa

Molins, Elies

Allin, Steven M.

McKee, Vickie

Bosch, Joan

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

[2] CSIC, Inst Ciencia Mat Barcelona, Cerdanyola Del Valles 08193, Spain

[3] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 14期

关键词：

D O I：

10.1021/jo070539g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5193 / 5201

页数：9

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