Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water

Reaction of α-substituted α-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05− 0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1−0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.


Published in:
Journal of the American Chemical Society, 136, 32, 11524-11528
Year:
2014
Publisher:
Washington, Amer Chemical Soc
ISSN:
1520-5126
Laboratories:




 Record created 2014-08-20, last modified 2018-03-17


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