期刊
CHIMIA
卷 69, 期 4, 页码 199-202出版社
SWISS CHEMICAL SOC
DOI: 10.2533/chimia.2015.199
关键词
Cinchona; Domino reaction; Isocyanoacetates; Oxidative MCR; Selenones
资金
- DSM
- Swiss Chemical Society
- EPFL
- Swiss National Science Foundation (SNCF)
- COST action [CM0905]
- Swiss State Secretariat for Education and Research (SER)
Bronsted base (Et3N or DBU) catalyzed Michael addition of a-substituted alpha-isocyanoacetates to phenyl vinyl selenones followed by a Bronsted 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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