A method for synthesis of cis-4-hydroxyproline analogs is described. A cis epoxide is converted to a cis-4-hydroxyproline, while the trans epoxide is converted into a ketone or α-aminolactone in the presence of Lewis and Brønsted acids. We propose the divergent chemoselectivity is controlled by H-bonding within the cis epoxide.
C. DaSilva, G. Mauk, L. Forshee, O. Pope, M. Doherty, M. Ongbongan, N. Lutz, Z. Kamanya, C. Bhatt, A. Braham, M. Kubek, S. Hawthorne, G. Campillo-Alvarado, A. Bhattacharjee, M. A. Bowring and R. V. O'Brien, Org. Biomol. Chem., 2025, Accepted Manuscript , DOI: 10.1039/D4OB01815J
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