Enantioselective Syntheses of α‐Silyl Amines via a Copper‐N‐Heterocyclic Carbene Catalyzed Nucleophilic Silicon Transfer to Imines. Issue 8 (20th June 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: 851
• Page End: 855
• Publication Date: 2014-06-20
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201402077
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>We developed an efficient and enantioselective method for the synthesis of chiral α‐silyl amines. In the presence of a copper(I)‐chiral monodentate N‐heterocyclic carbene complex (5 mol %), smooth nucleophilic silicon transfer from Me₂PhSiBpin (pin=pinacolato) to tosyl‐protected aldimines affords the corresponding α‐silyl amines in 77–93 % yields over 15 examples and satisfactory <italic>ee</italic> of 79–99 %. The asymmetric silylation of ketimines was also explored.</p> </abstract>