Chemodivergent synthesis of cis-4-hydroxyprolines from diastereomerically enriched epoxides

Clement DaSilva; Grace Mauk; Lucas Forshee; Oliver Pope; Mathilde Doherty; Max Ongbongan; Nicholas Lutz; Zemirah Kamanya; Kara Chris Bhatt; Andrew Braham; Miranda Kubek; Summer Hawthorne; Gonzalo Campillo-Alvarado; Avik Bhattacharjee; Miriam A. Bowring; Robert V. O'Brien

doi:10.1039/D4OB01815J

Chemodivergent synthesis of cis-4-hydroxyprolines from diastereomerically enriched epoxides†

Clement DaSilva,

^a Grace Mauk,^a Lucas Forshee,^a Oliver Pope,

^a Mathilde Doherty,

^a Max Ongbongan,

^a Nicholas Lutz,

^a Zemirah Kamanya,

^a Kara Chris Bhatt,

^a Andrew Braham,

^a Miranda Kubek,

^a Summer Hawthorne,

^a Gonzalo Campillo-Alvarado,

^a Avik Bhattacharjee,

^b Miriam A. Bowring

^a and Robert V. O'Brien

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Reed College, 3203 SE Woodstock Blvd, Portland, OR, USA
E-mail: obrienb@reed.edu

^b Department of Chemistry, York University, 4700 Keele St., Toronto, ON, Canada

Abstract

A method for synthesis of cis-4-hydroxyproline analogs is described. A cis epoxide is converted into 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.

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Organic & Biomolecular Chemistry

Chemodivergent synthesis of cis-4-hydroxyprolines from diastereomerically enriched epoxides†

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Chemodivergent synthesis of cis-4-hydroxyprolines from diastereomerically enriched epoxides

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