Asymmetric Catalytic [4 + 2] Cycloaddition via Cu–Allenylidene Intermediate: Stereoselective Synthesis of Tetrahydroquinolines Fused with a γ-Lactone Moiety.

A decarboxylative formal [4 + 2] cycloaddition reaction between ethynyl benzoxazinanones and 5-substituted 2-silyloxyfurans catalyzed by chiral Cu–Pybox complex is described. This method allows the formation of intriguing tetrahydroquinolines fused with a butyrolactone moiety featuring three contiguous chiral centers in high yields with excellent diastereo- and enantioselectivities in most cases. The utility of this method was exemplified by the removal of the N-protecting groups and derivatization on the terminal alkyne functionality of the cyclization products. [ABSTRACT FROM AUTHOR]