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Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins.

Abstract:

Lithium 2,2,6,6-tetramethylpiperidide (LTMP)-induced intramolecular cyclopropanation of unsaturated terminal epoxides provides an efficient and completely stereoselective entry to bicyclo[3.1.0]hexan-2-ols and bicyclo[4.1.0]heptan-2-ols. Further elaboration of C-5 and C-6 stannyl-substituted bicyclo[3.1.0]hexan-2-ols via Sn-Li exchange/electrophile trapping or Stille coupling generates a range of substituted bicyclic cyclopropanes. An alternative straightforward cyclopropanation protocol usin...

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Publication status:
Published

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Publisher copy:
10.1021/ja0672932

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Freixas, G More by this author
Kulikiewicz, KK More by this author
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Journal:
Journal of the American Chemical Society
Volume:
129
Issue:
14
Pages:
4456-4462
Publication date:
2007-04-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:e4e4ff0e-0250-4f22-9235-233fd6de55d0
Source identifiers:
33794
Local pid:
pubs:33794

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