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

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• 作者：Anna Andreou ; Jason Eames ; Majid Motevalli ; Timothy J. Prior ; Michael Watkinson
• 刊名：Tetrahedron Letters
• 出版年：2010
• 出版时间：10 March 2010
• 年：2010
• 卷：51
• 期：10
• 页码：1423-1425
• 全文大小：264 K

文摘

(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 30 % conversion). This desymmetrisation reaction is an example of a masked resolution.