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Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships

Abstract:

Templated tetrahydrofuran-based γ-azido esters were prepared with the C-2 and C-4 functionalities in cis and trans relative configurations. This was achieved by ring contraction of the suitably protected 2-O-triflates of pentono-1,5-lactones (d-ribose and l-arabinose) with subsequent introduction of the azide via the 4-O-triflate. Access to a corresponding β-azido ester was achieved in good yield. Little elimination product was observed by introduction of the azide via the 3-O-triflate. These...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2006.02.007

Authors


Edwards, AA More by this author
Sanjayan, GJ More by this author
Hachisu, S More by this author
Soengas, R More by this author
Stewart, A More by this author
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Journal:
TETRAHEDRON
Volume:
62
Issue:
17
Pages:
4110-4119
Publication date:
2006-04-24
DOI:
ISSN:
0040-4020
URN:
uuid:85ab9b6d-45c6-4c4c-8d49-c7b007060c79
Source identifiers:
39930
Local pid:
pubs:39930

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