Mn(III)-Mediated Reactions of Cyclopropanols with Vinyl Azides: Synthesis of Pyridine and 2-Azabicyclo[3.3.1]non-2-en-1-ol Derivatives
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- 17 August 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (35), 12570-12572
- https://doi.org/10.1021/ja905110c
Abstract
A Mn(III)-mediated divergent synthesis of substituted pyridines and 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives was exploited using readily available vinyl azides and cyclopropanols with a wide range of substituents. In short, the reactions of vinyl azides with monocyclic cyclopropanol provided pyridines in the presence of Mn(acac)3 (1.7 equiv), 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. These reactions may be initiated by a radical addition of β-keto radicals, generated by the one-electron oxidation of cyclopropanols, to vinyl azides to give iminyl radicals, which would cyclize with the intramolecular carbonyl groups. In addition, versatile transformations of 2-azabicyclo[3.3.1]non-2-en-1-ol to 2-azabicyclo[3.3.1]nonane or -non-2-nen frameworks were developed.This publication has 39 references indexed in Scilit:
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