Acetals of gamma-oxo-alpha,beta-unsaturated esters in nitrone cycloadditions. Regio- and stereochemical implications

Authors
Alibes, R Busque, F de March, P Figueredo, M Font, J Gambino, ME Keay, BA
Citation
R. Alibes et al., Acetals of gamma-oxo-alpha,beta-unsaturated esters in nitrone cycloadditions. Regio- and stereochemical implications, TETRAHEDR-A, 12(12), 2001, pp. 1747-1756
Citations number
42
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
12
Year of publication
2001
Pages
1747 - 1756
Database
ISI
SICI code
0957-4166(20010716)12:12<1747:AOGEIN>2.0.ZU;2-U
Abstract
Several acetals of gamma -oxo-alpha,beta -unsaturated esters have been prep ared, mainly from enantiopure C-2-symmetric diols, and their 1,3-dipolar cy cloaddition to 2,3,4,5-tetrahydropyridine 1-oxide has been studied. All the reactions showed complete regio selectivity and a high preference for the endo approach of the reactants in the transition state. The enantiopure ace tals derived from (cis, cis) -spiro [4.4]nonane- 1, 6-diol gave the highest diastereofacial selectivity. (C) 2001 Elsevier Science Ltd. All rights res erved.