Journal
SYNTHESIS-STUTTGART
Volume -, Issue 2, Pages 304-314Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1217126
Keywords
1,2-oxazines; carbene additions; cyclopropanes; ring enlargement; 1,2-oxazepines; palladium catalysis; alkynes
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Funding
- Deutsche Forschungsgemeinschaft
- Deutsche Akademische Austauschdienst
- Fonds der Chemischen Industrie
- Bayer Schering Pharma AG
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Dibromocarbene addition to D-glyceraldehyde-derived 1,2-oxazines syn-1 and anti-1 provided dibromocyclopropane intermediates syn-3 and anti-3, which smoothly reacted with methanol under ring enlargement to furnish 5-bromo-1,2-oxazepine derivatives syn-4 and anti-4. Related 1,2-oxazines such as arabinose-derived compounds furnished the 1,2-oxazepine derivatives syn-4e and anti-4f with fair efficacy. The alkenyl bromide moiety of 1,2-oxazepine derivatives syn-4 and anti-4 was then exploited for the introduction of new substituents via palladium-catalyzed C-C bond forming processes (Sonogashira, Suzuki, Stille, and Heck reactions). These transformations led to a series of new highly substituted 1,2-oxazepine derivatives syn-5 or anti-5-11 being of considerable interest for further synthetic elaborations.
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