Open AccessIntegrated 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
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.