Synthesis of enantiopure ethyl (1S,9aS)- and (1S,9aR)-1-phenyl-4,9-dioxohexahydropyrrolo[1,2-d][1,4] oxazepine-9a(7H)-carboxylate by carbenoid/ylide/Stevens-[1,2]-shift with ring enlargement

Authors
Chelucci, G Saba, A Valenti, R Bacchi, A
Citation
G. Chelucci et al., Synthesis of enantiopure ethyl (1S,9aS)- and (1S,9aR)-1-phenyl-4,9-dioxohexahydropyrrolo[1,2-d][1,4] oxazepine-9a(7H)-carboxylate by carbenoid/ylide/Stevens-[1,2]-shift with ring enlargement, TETRAHEDR-A, 11(16), 2000, pp. 3449-3453
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
16
Year of publication
2000
Pages
3449 - 3453
Database
ISI
SICI code
0957-4166(20000825)11:16<3449:SOEE(A>2.0.ZU;2-L
Abstract
Enantiomerically pure ethyl (1S,9aS)- and (1S,9aR)-1-phenyl-4,9-dioxohexahy dropyrrolo[1,2d][1,4]oxazepine-9a(7H)-carboxylate were obtained by Cu(II)-c atalyzed decomposition of an alpha-diazo carbonyl tethered to a chiral morp holinone. The reaction occurred with moderate diastereoselectivity but with complete enantioselectivity through the carbenoid/spiro-[5,6]-ammonium yli de/Stevens-[1,2]-shift with ring enlargement sequence. (C) 2000 Published b y Elsevier Science Ltd.