Issue 5, 2019

Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C–H insertion of cubane

Abstract

The first enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed. The key step was a telescoped Strecker reaction using (S)-2-amino-2-phenylethanol as a chiral auxiliary. Exploration of an alternative synthetic approach resulted in unprecedented cubane C–H insertion.

Graphical abstract: Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C–H insertion of cubane

Supplementary files

Article information

Article type
Communication
Submitted
27 Nov 2018
Accepted
22 Dec 2018
First published
15 Jan 2019

Org. Biomol. Chem., 2019,17, 1067-1070

Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C–H insertion of cubane

S. D. Houston, B. A. Chalmers, G. P. Savage and C. M. Williams, Org. Biomol. Chem., 2019, 17, 1067 DOI: 10.1039/C8OB02959H

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