Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 1988; 1988(12): 985-988
DOI: 10.1055/s-1988-27777
DOI: 10.1055/s-1988-27777
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Borane-Methyl Sulfide Reductive Cyclization of ω-Ester Alkylamides: A Convenient Synthesis of N-Substituted Cyclic Amines
Further Information
Publication History
Publication Date:
20 August 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/198812/lookinside/thumbnails/10.1055-s-1988-27777-1.jpg)
Borane-methyl sulfide (BMS) reduction of variously N-substituted succinamic and glutaramic esters affords the corresponding N-substituted pyrrolidines and piperidines in high yields. The limitations, mainly caused by steric hinderance around the amine nitrogen, and putative intermediates involved in this conversion, as detected by incomplete reaction and/or synthesis followed by BMS reduction, indicate that cyclization and amide reduction successfully compete with ester reduction to afford the N-substituted cyclized amines.