Cover Picture: Enantioselective Syntheses of α‐Silyl Amines via a Copper‐N‐Heterocyclic Carbene Catalyzed Nucleophilic Silicon Transfer to Imines (Asian J. Org. Chem. 8/2014). Issue 8 (August 2014)

• Record Type: Journal Article
• Authors: Zhao, Chunliang; Jiang, Chenran; Wang, Jing; Wu, Cai; Zhang, Qing‐Wei; He, Wei
• Is Part Of: Asian journal of organic chemistry. Volume 3:Issue 8(2014:Aug.)
• Page Start: 817
• Page End: 817
• Publication Date: 2014-08
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201490016
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Chiral α‐silyl amines</bold> are important bioactive agents as well as building blocks for the preparation of unnatural peptides and proteins. In their Communication paper on <ext-link ext-link-type="doi" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">page 851 ff, </ext-link> Wei He and co‐workers have developed an enantioselective synthesis of chiral α‐silyl amines via silylation of aldimines using the readily available CuCl/NaO<italic>t</italic>Bu/chiral‐N‐heterocyclic carbene catalyst system and the commercially available Suginome Me₂PhSiBpin reagent (pin=pinacolato). This method gives excellent enantiomeric excess up to 99% and has a wide substrate scope of 15 examples. The asymmetric silylation of ketimines was also explored.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh112x8wg0" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>