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J Org Chem. 2014 Apr 18;79(8):3671-7. doi: 10.1021/jo500300t. Epub 2014 Mar 31.

Asymmetric synthesis of protected α-amino boronic acid derivatives with an air- and moisture-stable Cu(II) catalyst.

Author information

1
Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Abstract

The asymmetric borylation of N-tert-butanesulfinyl imines with bis(pinacolato)diboron is achieved using a Cu(II) catalyst and provides access to synthetically useful and pharmaceutically relevant α-amino boronic acid derivatives. The Cu(II)-catalyzed reaction is performed on the benchtop in air at room temperature using commercially available, inexpensive reagents at low catalyst loadings. A variety of N-tert-butanesulfinyl imines, including ketimines, react readily to provide α-sulfinamido boronate esters in good yields and with high stereoselectivity. In addition, this transformation is applied to the straightforward, telescoped synthesis of α-sulfinamido trifluoroborates.

PMID:
24684495
DOI:
10.1021/jo500300t
[Indexed for MEDLINE]

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