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first enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed.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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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-01, Vol.17 (5), p.1067-1070
Main Authors: Houston, Sevan D, Chalmers, Benjamin A, Savage, G Paul, Williams, Craig M
Format: Article
Language:English
Subjects:
Cubane
Enantiomers
Insertion
NMR
Nuclear magnetic resonance
Phenylglycine
Rhodium
Synthesis
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Summary: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first enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed.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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02959h