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Asymmetric carbonyl-Ene and Friedel-Crafts reactions catalyzed by Lewis acid platinum group metal complexes of the enantiopure atropisomeric biaryl-like diphosphine (S)-Me₂-CATPHOS: a comparison with BINAP

Lookup NU author(s): Dr Simon DohertyORCiD, Dr Julian Knight, Hamid Mehdi-Zodeh

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Abstract

Lewis acid platinum and palladium complexes of (S)-Me₂-CATPHOS catalyze the carbonyl-ene reaction between allylbenzene derivatives and ethyl trifluoropyruvate to give the expected a-hydroxy esters with ee’s up to 97% while the corresponding reaction involving 2-allylfuran and thiophene were exclusively selective for Friedel-Crafts-type reactivity and gave the corresponding 2-hydroxy-trifluoromethyl ethyl esters in good yield and moderate to good enantioselectivity.

Publication metadata

Author(s): Doherty S, Knight JG, Mehdi-Zodeh H

Publication type: Article

Publication status: Published

Journal: Tetrahedron: Asymmetry

Year: 2012

Volume: 23

Issue: 3-4

Pages: 209-216

Print publication date: 29/02/2012

ISSN (print): 0957-4166

ISSN (electronic): 1362-511X

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/j.tetasy.2012.01.022

DOI: 10.1016/j.tetasy.2012.01.022

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