Silver(I)-Catalyzed Intramolecular Cyclizations of Epoxide-Propargylic Esters to 1,4-Oxazine Derivatives.
An interesting silver(I)-catalyzed, one-pot intramolecular cyclization of epoxide-propargylic esters is described. A variety of 1,4-oxazine derivatives were obtained through a novel domino sequence, including three-membered ring-opening, 3,3-sigmatropic rearrangement, 6-exo-cycloisomerization and subsequent intramolecular elimination in moderate yields under mild conditions.
Key Laboratory for Advanced Materials and Institute of Fine Chemicals School of Chemistry and Molecule Engineering East China University of Science and Technology 130 Mei Long Road Shanghai 200237 P. R. China.
Peng-Hua
PH
Li
Key Laboratory for Advanced Materials and Institute of Fine Chemicals School of Chemistry and Molecule Engineering East China University of Science and Technology 130 Mei Long Road Shanghai 200237 P. R. China.
Jin-Ming
JM
Yang
State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences 345 Linglin Lu Shanghai 200032 P. R. China.
Yin
Y
Wei
Key Laboratory for Advanced Materials and Institute of Fine Chemicals School of Chemistry and Molecule Engineering East China University of Science and Technology 130 Mei Long Road Shanghai 200237 P. R. China; State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences 345 Linglin Lu Shanghai 200032 P. R. China.
Min
M
Shi
cyclization; epoxides; propargylic ester; silver catalysis; tandem reaction