Mn(III)-Mediated Reactions of Cyclopropanols with Vinyl Azides: Synthesis of Pyridine and 2-Azabicyclo[3.3.1]non-2-en-1-ol Derivatives

Yi-Feng Wang and Shunsuke Chiba*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore, Email: shunsukentu.edu.sg

Y.-F. Wang, S. Chiba, J. Am. Chem. Soc., 2009, 131, 12570-12572.

DOI: 10.1021/ja905110c

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Abstract

Reactions of vinyl azides with monocyclic cyclopropanols provided pyridines in the presence of Mn(acac)₃, whereas those with bicyclic cyclopropanols led to the formation of 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives using a catalytic amount of Mn(acac)₃.

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Key Words

pyridines, cyclopropanols, vinyl azides, manganese(III)

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ID: J48-Y2009-2650