A. Al‐Harrasi, S. Fischer, R. Zimmer*
2010
Citations
0
Influential Citations
7
Citations
Journal
Synthesis
Abstract
Dibromocarbene addition to D-glyceraldehyde-derived 1,2 -oxazines SYN-1 and ANTI-1 provided dibromocyclopropane intermediates SYN- 3 and ANTI- 3, whichsmoothly reacted with methanol under ring enlargement to furnish5-bromo-1,2 -oxazepine derivatives SYN-4 and ANTI-4. Related1,2-oxazines such as arabinose-derived- compounds furnishedthe 1,2-oxazepine derivatives SYN- 4E and ANTI- 4F with fair efficacy. The alkenyl bromidemoiety of 1,2-oxazepine derivatives SYN-4 and ANTI-4 was then exploited for the introductionof new substituents via palladium-catalyzed C-C bond formingprocesses (Sonogashira, Suzuki, Stille, and Heck reactions). Thesetransformations led to a series of new highly substituted 1,2-oxazepinederivatives SYN- 5 or ANTI- 5- 11 being of considerable interest for furthersynthetic elaborations.