Anomalies in the Stereoselectivity of the Petasis Reaction Using Styrenyl Boronic Acids
Quentin I. Churches A , James K. Johnson A , Nathan L. Fifer A and Craig A. Hutton A BA School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Vic. 3010, Australia.
B Corresponding author. Email: chutton@unimelb.edu.au
Australian Journal of Chemistry 64(1) 62-67 https://doi.org/10.1071/CH10341
Submitted: 14 September 2010 Accepted: 1 December 2010 Published: 14 January 2011
Abstract
The Petasis three-component coupling reaction of N-benzylphenylglycinol, glyoxylic acid, and styrenylboronic acids allows for the efficient synthesis of functionalized homoarylalanine derivatives. The reactions were shown to proceed in high yield but low selectivity, regardless of the nature of the substituent on the styrenylboronic acid component. Anomalies in the stereoselectivity of these reactions compared with previously reported results have been traced to the source of the organoboronic acid. Asymmetric dihydroxylation of the unsaturated amino acid derivatives enables a highly efficient route to dihydroxyhomoarylalanine derivatives.
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