Elżbieta Wojaczyńska, I. Turowska-Tyrk, J. Skarżewski
Sep 23, 2012
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0
Influential Citations
19
Citations
Journal
Tetrahedron
Abstract
The reaction of 2-azanorbornan-3-yl methanols under Mitsunobu or mesylation conditions with various nucleophiles led to a series of chiral-bridged azepanes with configuration at C-4 dependent on the configuration of the starting alcohol. High yielding, stereoselective ring expansion to novel 2-azabicyclo[3.2.1]octane system occurred via aziridinium intermediates, which were specifically opened by nucleophilic attack at the more substituted carbon.