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Radical deoxygenation of 3-azatricyclo[2.2.1.0(2,6)]heptan-5-ols to 2-azabicyclo[2.2.1]hept-5-enes and 1,2-dihydropyridines

Abstract:
Additions of alkyl or aryl Grignard reagents, or pyridin-3-yl-lithiums or lithium alkoxides, to exo-5,6-epoxy-7-(tert-butoxycarbonyl)-2-tosyl-7-azabicyclo[2.2.1]hept-2-ene lead to 7-substituted-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols. Radical deoxygenations of 7-alkyl-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols give 7-alkyl-4-tosyl-2-azabicyclo[2.2.1]hept-5-enes, whereas 7-aryl-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols give 2-(arylmethyl)-5-tosyl-1,2-dihydropyridines. © 2009 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Publisher copy:
10.1016/j.tet.2009.07.022

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Maxwell, CR More by this author
Cowley, AR More by this author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Inorganic Chemistry
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Journal:
TETRAHEDRON
Volume:
65
Issue:
37
Pages:
7825-7836
Publication date:
2009-09-12
DOI:
ISSN:
0040-4020
URN:
uuid:cbb82642-ea96-4727-9b5d-8d3824c5d91f
Source identifiers:
41337
Local pid:
pubs:41337
Language:
English

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