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Issue 8, 2010
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Stereoselectivity induced by support confinement effects. Aza-pyridinoxazolines: A new family of C1-symmetric ligands for copper-catalyzed enantioselective cyclopropanation reactions

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Abstract

Aza-pyridinoxazoline ligands, a new class of C1-symmetric ligands, are described and tested in the heterogeneous enantioselective catalysis of a cyclopropanation reaction, with the aim of improving surface confinement effects by the clay support on the reaction stereoselectivity. In the case of trans/cis diastereoselectivity, these surface effects lead to a systematic reversal of selectivity, cis-cyclopropanes being favored. Regarding the enantioselectivities, support confinement has a positive effect in the case of major cis-cyclopropane products, leading to moderate enantioselectivity values (60% ee). A theoretical (DFT) mechanistic study is carried out to explain the origin of the enantioselectivity in the homogeneous phase at a molecular level, and to get insights on the geometries of the key intermediates and transition structures.

Graphical abstract: Stereoselectivity induced by support confinement effects. Aza-pyridinoxazolines: A new family of C1-symmetric ligands for copper-catalyzed enantioselective cyclopropanation reactions

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Article information


Submitted
16 Sep 2009
Accepted
04 Dec 2009
First published
14 Jan 2010

Dalton Trans., 2010,39, 2098-2107
Article type
Paper

Stereoselectivity induced by support confinement effects. Aza-pyridinoxazolines: A new family of C1-symmetric ligands for copper-catalyzed enantioselective cyclopropanation reactions

J. I. García, G. Jiménez-Osés, B. López-Sánchez, J. A. Mayoral and A. Vélez, Dalton Trans., 2010, 39, 2098
DOI: 10.1039/B919274C

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