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Isothiourea-mediated asymmetric O- to C-carboxyl transfer of oxazolyl carbonates: structure-selectivity profiles and mechanistic studies

Joannesse, Caroline, Johnston, Craig P., Morrill, Louis, Woods, Philip A., Kieffer, Madeleine, Nigst, Tobias A., Mayr, Herbert, Lebl, Tomas, Philp, Douglas, Bragg, Ryan A. and Smith, Andrew D. 2012. Isothiourea-mediated asymmetric O- to C-carboxyl transfer of oxazolyl carbonates: structure-selectivity profiles and mechanistic studies. Chemistry - a European Journal 18 (8) , pp. 2398-2408. 10.1002/chem.201102847

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Abstract

The structural motif within a series of tetrahydropyrimidine-based isothioureas necessary for generating high asymmetric induction in the asymmetric Steglich rearrangement of oxazolyl carbonates is fully explored, with crossover and dynamic 19F NMR experiments used to develop a mechanistic understanding of this transformation.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: Article first published online: 19 January 2012
Publisher: WileyBlackwell
ISSN: 0947-6539
Last Modified: 04 Jun 2017 08:12
URI: http://orca.cf.ac.uk/id/eprint/74302

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