Enantiodivergent Deprotonation/Acylation of α‐Amino Nitriles1. Issue 49 (9th October 2013)

• Record Type: Journal Article
• Authors: Sasaki, Michiko; Takegawa, Tomo; Sakamoto, Kunihiro; Kotomori, Yuri; Otani, Yuko; Ohwada, Tomohiko; Kawahata, Masatoshi; Yamaguchi, Kentaro; Takeda, Kei
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 49(2013)
• Page Start: 12956
• Page End: 12960
• Publication Date: 2013-10-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201306443
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Back to 'base'ics</bold>: The title reaction of enantioenriched α‐ureidonitriles was found to proceed in a highly enantiodivergent manner despite the intermediacy of stereolabile α‐nitrile metallocarbanions. Enantiodivergence is dependent upon the base used. For the less basic hexamethyldisilazides (HMDS), deprotonation in which a metal (M) cation is precomplexed with an electrophile is proposed. LDA=lithium diisopropylamide.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t79zw9b" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>