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Synfacts 2009(10): 1122-1122  
DOI: 10.1055/s-0029-1217847
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Unprecedented Reactivity in Nucleophilic Ring Opening of Oxabicycles

Contributor(s): Mark Lautens, David A. Candito
C. S. Schindler, S. Diethelm, E. M. Carreira*
ETH Zürich, Switzerland
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

The authors report novel reactivity for oxabicyclo[2.2.1]heptenes and -heptanes where nucleophilic attack occurs at the bridge-head position to yield heterocyclic structures in a stereospecific manner. When this methodology is combined with stereoselective methods available for making the precursor oxabicycles the result is a powerful method for making stereochemically rich heterocycles.