Enantioselective Addition of Silicon Nucleophiles to Aldimines Using a Preformed NHC–Copper(I) Complex as the Catalyst1. Issue 19 (3rd April 2014)

• Record Type: Journal Article
• Authors: Hensel, Alexander; Nagura, Kazuhiko; Delvos, Lukas B.; Oestreich, Martin
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 19(2014)
• Page Start: 4964
• Page End: 4967
• Publication Date: 2014-04-03
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201402086
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A remaining major challenge in the asymmetric addition of silicon nucleophiles to typical prochiral acceptors, the enantioselective 1, 2‐addition to aldimines, is addressed. Activation of the SiB bond in the silicon pronucleophile by a copper(I) alkoxide with McQuade's chiral six‐membered N‐heterocyclic carbene as a supporting ligand releases the silicon nucleophile, which adds to various aldimines with high levels of enantioselectivity. The new method provides a catalytic asymmetric access to α‐silylated amines.</p> </abstract>