Skip to main content

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

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

Authors

Anna Andreou

Jason Eames J.Eames@hull.ac.uk

Majid Motevalli

Michael Watkinson



Abstract

(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.

Journal Article Type Article
Publication Date Mar 10, 2010
Journal TETRAHEDRON LETTERS
Print ISSN 0040-4039
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 51
Issue 10
Pages 1423-1425
APA6 Citation 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. https://doi.org/10.1016/j.tetlet.2010.01.019
DOI https://doi.org/10.1016/j.tetlet.2010.01.019
Keywords Organic Chemistry; Biochemistry; Drug Discovery
Publisher URL https://www.sciencedirect.com/science/article/pii/S0040403910000481?via%3Dihub
;