Improvement of the Synthesis of Chiral Non-Racemic Bicyclic Lactams in the Piperidin-2-ones Series
- 1 April 1996
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 26 (8) , 1605-1611
- https://doi.org/10.1080/00397919608003529
Abstract
Bicyclic lactams 8 have been prepared in enantiomerically pure form from the corresponding amino esters 5 and glutaric anhydride. The key step is the reduction of imides 7 in methanol. Selective reduction of 8 furnished N-substituted lactams 9.Keywords
This publication has 8 references indexed in Scilit:
- Asymmetric synthesis. XXXV1. Synthesis of 2-methyl 5-substituted substituted piperidines from chiral non-racemic lactamsTetrahedron Letters, 1995
- Asymmetric synthesis. XXX. Synthesis of 3-substituted piperidines from chiral non-racemic lactamsTetrahedron Letters, 1994
- A New Potential Acyl Iminium Ion for the Asymmetric Synthesis of Piperidine DerivativesHETEROCYCLES, 1993
- Chiral non-racemic bicyclic lactams. Vehicles for the construction of natural and unnatural products containing quaternary carbon centers.Tetrahedron, 1991
- A facile synthesis of chiral bicyclic lactams utilized in the formation of chiral quaternary carbon compoundsThe Journal of Organic Chemistry, 1989
- Synthesis and absolute configuration of the Aristotelia alkaloid peduncularineJournal of the American Chemical Society, 1989
- Cationic cyclization of ketene dithioacetals. A general synthesis of pyrrolizidine, indolizidine, and quinolizidine alkaloid ring systemsThe Journal of Organic Chemistry, 1984
- NaBH4 reduction of cyclic imidesTetrahedron, 1975