Studies in Lewis acid and LiClO4 (or Nafion-H) catalysed ionic Diels- Alder reactions of chiral and achiral olefinic acetals respectively

R. Kumareswaran, Padmar S. Vankar, M. Venkat Ram Reddy, Sangeeta V. Pitre, Roy Raja, Yashwant D. Vankar

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Abstract

Chiral olefinic acetals derived from crotonaldehyde undergo ionic Diels- Alder reaction giving the corresponding cycloadducts in moderate to good diastereoselectivities. A variety of achiral olefinic acetals react with isoprene and cyclopentadiene to form the cycloadducts in good to excellent yields when catalysed by 4M LiClO4 in nitromethane or by Nafion-H in dichloromethane.

Original languageEnglish (US)
Pages (from-to)1099-1110
Number of pages12
JournalTetrahedron
Volume55
Issue number4
DOIs
StatePublished - Jan 22 1999

Bibliographical note

Funding Information:
We thank the Department of Science and Technology, New Delhi, for financial support through a project (No. SP/S1/G-22/91). One of us (R. Kumareswaran) thanks the Council of Scientific and Industrial Research, New Delhi, for the award of a Senior Research Fellowship. We thank Profs. G.A. Olah and G.K.S. Prakash for the gift of Nation K.

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