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Issue 5, 2019
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Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C–H insertion of cubane

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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first enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed.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

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Article information


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

Org. Biomol. Chem., 2019,17, 1067-1070
Article type
Communication

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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