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

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enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed.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

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Veröffentlicht in:	Organic & biomolecular chemistry 2019-01, Vol.17 (5), p.1067-1070
Hauptverfasser:	Houston, Sevan D, Chalmers, Benjamin A, Savage, G Paul, Williams, Craig M
Format:	Artikel
Sprache:	eng
Schlagworte:	Cubane Enantiomers Insertion NMR Nuclear magnetic resonance Phenylglycine Rhodium Synthesis
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creator	Houston, Sevan D Chalmers, Benjamin A Savage, G Paul Williams, Craig M
description	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first enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed.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.
doi_str_mv	10.1039/c8ob02959h
format	Article
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source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Cubane Enantiomers Insertion NMR Nuclear magnetic resonance Phenylglycine Rhodium Synthesis
title	Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C-H insertion of cubane
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