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Synthesis of pseudo-geminal-, pseudo-ortho-, and ortho-phosphinyl-oxazolinyl-[2.2]paracyclophanes for use as ligands in asymmetric catalysis.

Whelligan, DK and Bolm, C (2006) Synthesis of pseudo-geminal-, pseudo-ortho-, and ortho-phosphinyl-oxazolinyl-[2.2]paracyclophanes for use as ligands in asymmetric catalysis. J Org Chem, 71 (12). 4609 - 4618. ISSN 0022-3263

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Abstract

Syntheses of three regioisomers of aromatic-substituted phosphinyl-oxazolinyl-[2.2]paracyclophanes, pseudo-geminal, pseudo-ortho, and ortho, have been carried out or, in the latter two cases, newly developed. It has, therefore, been demonstrated that all aromatic-substituted isomers relevant for use as chelating ligands for asymmetric catalysis are accessible. These P,N-ligands, along with their diastereoisomers, were shown to exhibit widely differing activity and enantioselectivity (up to 89% ee) in the Pd-catalyzed asymmetric allylic alkylation reaction.

Item Type: Article
Additional Information: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry copyright © American Chemical Society after peer review and technical editing by the publisher.To access the final edited and published work see http://dx.doi.org/10.1021/jo060668h.
Divisions: Faculty of Engineering and Physical Sciences > Chemistry
Depositing User: Symplectic Elements
Date Deposited: 24 May 2012 12:23
Last Modified: 23 Sep 2013 19:14
URI: http://epubs.surrey.ac.uk/id/eprint/227185

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