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Synthesis 2010(2): 304-314  
DOI: 10.1055/s-0029-1217126
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Ring Enlargement of Carbohydrate-Derived 1,2-Oxazines to Enantiopure 5-Bromo-1,2-oxazepines and Subsequent Palladium-Catalyzed Reactions

Ahmed Al-Harrasia,b, Sebastian Fischera, Reinhold Zimmera, Hans-Ulrich Reissig*a
a Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany
Fax: +49(30)83855367; e-Mail: hans.reissig@chemie.fu-berlin.de;
b Department of Chemistry, College of Science, Sultan Qaboos University, Alkhod 123, Sultanate of Oman
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Publication History

Received 14 August 2009
Publication Date:
20 November 2009 (online)

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Abstract

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.

Key words

1,2-oxazines - carbene additions - cyclopropanes - ring enlargement - 1,2-oxazepines - palladium catalysis - alkynes

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