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

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.


Published in:
CHIMIA International Journal for Chemistry, 69, 4, 199-202
Year:
2015
Publisher:
Bern, Schweizerische Chemische Gesellschaft
ISSN:
0009-4293
Keywords:
Laboratories:




 Record created 2015-05-05, last modified 2018-12-03


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