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:	Creators Email Pitt Username ORCID Wipf, P pwipf@pitt.edu PWIPF 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:	12 Jun 2021 22:55
URI:	http://d-scholarship-dev.library.pitt.edu/id/eprint/25723

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