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Desymmetrisation of (4R,5S)-4,5-diphenylimidazolidine-2-thione using pentafluorophenyl active esters

Andreou, Anna; Eames, Jason; Motevalli, Majid; Prior, Timothy J.; Watkinson, Michael


Anna Andreou

Jason Eames

Majid Motevalli

Michael Watkinson


(4R,5S)-4,5-Diphenylimidazolidine-2-thione is efficiently desymmetrised by stereorandom deprotonation with NaHMDS, followed by kinetic resolution of the resulting racemic intermediate with an enantiomerically pure pentafluorophenyl active ester. The levels of diastereocontrol were found to be excellent (86-92% de at similar to 30% conversion). This desymmetrisation reaction is an example of a masked resolution. (C) 2010 Elsevier Ltd. All rights reserved.


Andreou, A., Eames, J., Motevalli, M., Prior, T. J., & Watkinson, M. (2010). Desymmetrisation of (4R,5S)-4,5-diphenylimidazolidine-2-thione using pentafluorophenyl active esters. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 51(10), 1423-1425.

Journal Article Type Article
Acceptance Date Jan 8, 2010
Online Publication Date Jan 13, 2010
Publication Date Mar 10, 2010
Print ISSN 0040-4039
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 51
Issue 10
Pages 1423-1425
Keywords Organic Chemistry; Biochemistry; Drug Discovery
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