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Houston SD, Chalmers BA, Savage GP, et al. Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C-H insertion of cubane. Org Biomol Chem. 2019;17(5):1067-1070doi: 10.1039/c8ob02959h.
Houston, S. D., Chalmers, B. A., Savage, G. P., & Williams, C. M. (2019). Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C-H insertion of cubane. Organic & biomolecular chemistry, 17(5), 1067-1070. https://doi.org/10.1039/c8ob02959h
Houston, Sevan D, et al. "Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C-H insertion of cubane." Organic & biomolecular chemistry vol. 17,5 (2019): 1067-1070. doi: https://doi.org/10.1039/c8ob02959h
Houston SD, Chalmers BA, Savage GP, Williams CM. Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C-H insertion of cubane. Org Biomol Chem. 2019 Jan 31;17(5):1067-1070. doi: 10.1039/c8ob02959h. PMID: 30644962.
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Org Biomol Chem. 2019 Jan 31;17(5):1067-1070. doi: 10.1039/c8ob02959h.

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

Organic & biomolecular chemistry

Sevan D Houston, Benjamin A Chalmers, G Paul Savage, Craig M Williams

Affiliations

  1. School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland, Australia. [email protected].

PMID: 30644962 DOI: 10.1039/c8ob02959h

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enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed.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

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