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Zirconocene-catalyzed cationic Diels-Alder reactions

Wipf, P and Xu, W (1995) Zirconocene-catalyzed cationic Diels-Alder reactions. Tetrahedron, 51 (15). 4551 - 4562. ISSN 0040-4020

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Abstract

In situ prepared Cp2ZrCl⊕ catalyzes the formation of dioxolenium ions from α,β-unsaturated epoxy esters. As a consequence of this activation process, acrylate, methacrylate and crotonate derivatives undergo a rapid and stereoselective cationic [4+2] cycloaddition with a wide range of dienes. Ring-extended carboxylic acid derivatives are formed in 1-7 h at 0-21 °C and in 50-90% yield after saponification of the intermediate diol esters. Simple Lewis acid catalysis by Cp2ZrCl⊕ can be excluded on the basis of the experimental results. © 1995.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Xu, W
Date: 10 April 1995
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 51
Number: 15
Page Range: 4551 - 4562
DOI or Unique Handle: 10.1016/0040-4020(94)01140-u
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
Date Deposited: 06 Oct 2015 14:56
Last Modified: 02 Feb 2019 15:56
URI: http://d-scholarship.pitt.edu/id/eprint/25723

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