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

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

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.

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

• Journal Article Type: Article
• Acceptance Date: Jan 8, 2010
• Online Publication Date: Jan 13, 2010
• 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
• DOI: https://doi.org/10.1016/j.tetlet.2010.01.019
• Keywords: Organic Chemistry; Biochemistry; Drug Discovery
• Public URL: https://hull-repository.worktribe.com/output/391434
• Publisher URL: https://www.sciencedirect.com/science/article/pii/S0040403910000481?via%3Dihub