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

Joannesse, Caroline, Johnston, Craig P., Morrill, Louis ORCID: https://orcid.org/0000-0002-6453-7531, 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:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Additional Information:	Article first published online: 19 January 2012
Publisher:	WileyBlackwell
ISSN:	0947-6539
Last Modified:	28 Oct 2022 09:22
URI:	https://orca.cardiff.ac.uk/id/eprint/74302

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