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

Buyck, ThomasWang, QianZhu, Jieping2015-05-052015-05-052015-05-05201510.2533/chimia.2015.199https://infoscience.epfl.ch/handle/20.500.14299/113697WOS:000354507200009Brønsted 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.CinchonaDomino reactionIsocyanoacetatesOxidative MCRSelenonesIntegrated One-Pot Synthesis of 1,3-Oxazinan-2-ones from Isocyanoacetates and Phenyl Vinyl Selenonestext::journal::journal article::research article