This work was supported by an ETH Research Grant (ETH-12 11-1). We are grateful to Drs. Xiangyang Zhang and Bernd Schweizer of ETH (Zürich) for mass spectrometry and for X-ray crystallographic structural determination. SnAP=tin (Sn) amine protocol.
SnAP Reagents for the Transformation of Aldehydes into Substituted Thiomorpholines—An Alternative to Cross-Coupling with Saturated Heterocycles†
Article first published online: 23 DEC 2012
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 6, pages 1705–1708, February 4, 2013
How to Cite
Vo, C.-V. T., Mikutis, G. and Bode, J. W. (2013), SnAP Reagents for the Transformation of Aldehydes into Substituted Thiomorpholines—An Alternative to Cross-Coupling with Saturated Heterocycles . Angew. Chem. Int. Ed., 52: 1705–1708. doi: 10.1002/anie.201208064
- Issue published online: 1 FEB 2013
- Article first published online: 23 DEC 2012
- Manuscript Received: 7 OCT 2012
- ETH Research Grant. Grant Number: ETH-12 11-1
- nitrogen heterocycles;
- radical reactions;
It's a SnAP! The transformation of aldehydes into N-unsubstituted 3-thiomorpholines provides a convenient alternative to metal-catalyzed cross-coupling reactions, which are generally unsuited to the functionalization of saturated N-heterocycles. A copper-mediated radical cyclization is the key to the mild conditions, high functional group tolerance, and broad substrate scope offered by these reagents.