Palladium-Catalyzed Stereoselective Allylaminocyclization and 1,3-Butadien-2-ylaminocyclization of Allenyl Tosylcarbamates

Article abstract of DOI:10.1021/jo00117a031

Palladium , in the presence of a base (Et3N or K2CO3) in THF at room temperature, catalyzes an allylaminocyclization of 2,3-butadienyl tosylcarbamates 1 with allylic chlorides to selectively provide trans-4,5-disubstituted 2-oxazolidinones 2 in good yields.Under similar conditions, Pd(PPh3)4 catalyzes an N-allylation of 1 to give 3.A limited number of 3,4-pentadienyl tosylcarbamates 5 undergo the allylaminocyclization to provide tetrahydro-1,3-oxazin-2-ones 6.In the absence of an allylic chloride, Pd(PPh3)4 and PdCl2(PhCN)2 catalyze a formal dimerization of 1 to provide C4-triene-substituted 2-oxazolidinones 4 in moderate to good yields.