Part 4 in the series "Studies in asymmetric synthesis" - Studies in Lewis acid and LiClO4 (or Nafion-H) catalysed ionic Diels-Alder reactions of chiral and achiral olefinic acetals respectively

Authors
Kumareswaran, R Vankar, PS Reddy, MVR Pitre, SV Roy, R Vankar, YD
Citation
R. Kumareswaran et al., Part 4 in the series "Studies in asymmetric synthesis" - Studies in Lewis acid and LiClO4 (or Nafion-H) catalysed ionic Diels-Alder reactions of chiral and achiral olefinic acetals respectively, TETRAHEDRON, 55(4), 1999, pp. 1099-1110
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
4
Year of publication
1999
Pages
1099 - 1110
Database
ISI
SICI code
0040-4020(19990122)55:4<1099:P4ITS">2.0.ZU;2-6
Abstract
Chiral olefinic acetals derived from crotonaldehyde undergo ionic Diets-Ald er reaction giving the corresponding cycloadducts in moderate to good diast ereoselectivities. A variety of achiral olefinic acetals react with isopren e and cyclopentadiene to form the cycloadducts in good to excellent yields when catalysed by 4M LiClO4 in nitromethane or by Nafion-H in dichlorometha ne. (C) 1999 Elsevier Science Ltd. All rights reserved.