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Gosteli-Claisen Rearrangement: Substrate Synthesis, Simple Diastereoselectivity, and Kinetic Studies

Rehbein, Julia, Leick, S. and Hiersemann, M. 2009. Gosteli-Claisen Rearrangement: Substrate Synthesis, Simple Diastereoselectivity, and Kinetic Studies. Journal of Organic Chemistry 74 (4) , pp. 1531-1540. 10.1021/jo802303m

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Abstract

The results of kinetic studies on the uncatalyzed [3,3]-sigmatropic rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers are reported. Apparently first reported by Gosteli in 1972, this variation of a Claisen rearrangement enjoyed a shadowy existence for three decades until its potential for the development of a catalytic asymmetric Claisen rearrangement was discovered. Inspired by this development, we have studied substituent and solvent rate effects, and we provide evidence that a chairlike transition state is highly favorable for the uncatalyzed Gosteli−Claisen rearrangement.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: ACS
ISSN: 0022-3263
Last Modified: 19 Mar 2016 22:21
URI: http://orca-mwe.cf.ac.uk/id/eprint/13003

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