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

IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2025-02-21 DOI:10.1039/d4ob01815j
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
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引用次数: 0

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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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
期刊最新文献
Chemodivergent synthesis of cis-4-hydroxyprolines from diastereomerically enriched epoxides. First synthesis of (difluoroiodomethyl)thiophenes through double iodation of 2-(difluoromethylene)but-3-yn-1-yl benzyl sulfides. HFIP-promoted phosphorylation of indol-3-yl methanols to access (indol-3-yl)methyl phosphonates. PIDA mediated oxidative annulation of aryl methyl ketones: a facile approach for the chemoselective synthesis of 5-substituted oxazoles. Pretzelanes, [1]rotaxanes and molecular figures-of-eight - crossing the bridge from fundamentals to functional applications.
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