1099-0690/asset/2046_left.gif?v=1&s=0ec9ed8843eb5403f667ad940f5a1c68cb5ef011)
1099-0690/asset/2046_right.gif?v=1&s=b2caf576ff74b55a6a4748bd86a910901b664c52)
Full Paper
Studies on the Diastereoselective Intramolecular Pauson–Khand Reaction on Regioisomeric Chiral Perhydrobenzoxazines Derived from (–)-8-Aminomenthol
Article first published online: 27 DEC 2011
DOI: 10.1002/ejoc.201101462
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Maestro, A., Pedrosa, R., Pérez-Encabo, A. and Pérez-Rueda, J. J. (2012), Studies on the Diastereoselective Intramolecular Pauson–Khand Reaction on Regioisomeric Chiral Perhydrobenzoxazines Derived from (–)-8-Aminomenthol. Eur. J. Org. Chem., 2012: 1202–1208. doi: 10.1002/ejoc.201101462
Publication History
- Issue published online: 13 FEB 2012
- Article first published online: 27 DEC 2011
- Manuscript Received: 7 OCT 2011
Funded by
- Ministerio de Ciencia e Innovacion (MICINN). Grant Numbers: CTQ2005-01191/BQU, CTQ2008-03960/BQU
- Junta de Castilla y León. Grant Number: 168
- Ministerio de Educación y Ciencia (MEC)
Keywords:
- Asymmetric synthesis;
- Cyclization;
- Enynes;
- Stereoselective synthesis
Abstract
Chiral perhydrobenzoxazines derived from (–)-8-aminomenthol and containing a 1,6-enyne moiety participate in intramolecular diastereoselective Pauson–Khand reactions with diastereoselection that depends on the nature of the starting compounds. 3-Propargyl-2-vinyl-substituted perhydrobenzoxazines yielded the cyclization products with low diastereoselectivity except for compounds where the double bond was 1,2-disubstituted. Regioisomeric perhydrobenzoxazines with the acetylenic bond at C-2 and an allyl substituent at the nitrogen atom gave much better stereochemical discrimination.