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

doi:10.1016/S0040-4020(98)01088-6

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

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

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 language	English (US)
Pages (from-to)	1099-1110
Number of pages	12
Journal	Tetrahedron
Volume	55
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4020(98)01088-6
State	Published - 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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title = "Studies in Lewis acid and LiClO4 (or Nafion-H) catalysed ionic Diels- Alder reactions of chiral and achiral olefinic acetals respectively",

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.",

author = "R. Kumareswaran and Vankar, {Padmar S.} and Reddy, {M. Venkat Ram} and Pitre, {Sangeeta V.} and Roy Raja and Vankar, {Yashwant D.}",

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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T1 - Studies in Lewis acid and LiClO4 (or Nafion-H) catalysed ionic Diels- Alder reactions of chiral and achiral olefinic acetals respectively

AU - Kumareswaran, R.

AU - Vankar, Padmar S.

AU - Reddy, M. Venkat Ram

AU - Pitre, Sangeeta V.

AU - Raja, Roy

AU - Vankar, Yashwant D.

N1 - 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.

PY - 1999/1/22

Y1 - 1999/1/22

N2 - 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.

AB - 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.

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