G. Chelucci, A. Saba, R. Valenti
Aug 25, 2000
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract Enantiomerically pure ethyl (1 S ,9a S )- and (1 S ,9a R )-1-phenyl-4,9-dioxohexahydropyrrolo[1,2- d ][1,4]oxazepine-9a(7 H )-carboxylate were obtained by Cu(II)-catalyzed decomposition of an α-diazo carbonyl tethered to a chiral morpholinone. The reaction occurred with moderate diastereoselectivity but with complete enantioselectivity through the carbenoid/spiro-[5,6]-ammonium ylide/Stevens-[1,2]-shift with ring enlargement sequence.