Integrated One-Pot Synthesis of 1,3-Oxazinan-2-ones from Isocyanoacetates and Phenyl Vinyl Selenones | Zendy

Thomas Buyck | Zendy; Qian Wang | Zendy; Jieping Zhu | Zendy

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Integrated One-Pot Synthesis of 1,3-Oxazinan-2-ones from Isocyanoacetates and Phenyl Vinyl Selenones

Author(s) -

Thomas Buyck,

Qian Wang,

Jieping Zhu

Publication year - 2015

Publication title -

chimia international journal for chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.387

H-Index - 55

eISSN - 2673-2424

pISSN - 0009-4293

DOI - 10.2533/chimia.2015.199

Subject(s) - bifunctional , domino , cinchona , catalysis , brønsted–lowry acid–base theory , chemistry , leaving group , organic chemistry , michael reaction , activator (genetics) , base (topology) , cinchona alkaloids , combinatorial chemistry , medicinal chemistry , enantioselective synthesis , mathematics , biochemistry , mathematical analysis , gene

Brønsted base (Et3N or DBU) catalyzed Michael addition of α-substituted α-isocyanoacetates to phenyl vinyl selenones followed by a Brønsted acid (PTSA) catalyzed domino oxidative cyclization afforded 1,3-oxazinan-2-ones in good to excellent yields. Enantio-enriched 1,3-oxazinan-2-ones were accessible using a Cinchona alkaloid-derived bifunctional catalyst for the first step. In this integrated one-pot process, the phenyl selenonyl group acted consecutively as an activator, a leaving group and a latent oxidant.

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