Issue 15, 1999
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols

Simon B. Bedford,   Kathryn E. Bell,   Frank Bennett,   Christopher J. Hayes,   David W. Knight  and  Duncan E. Shaw  

Abstract

Overall 5-endo-trig iodocyclizations of homoallylic alcohols, with a range of substitution patterns, leading to β-iodotetrahydrofurans are usually highly efficient and stereoselective when carried out in anhydrous acetonitrile in the presence of sodium hydrogen carbonate. Such cyclizations, which are not exceptions to Baldwin’s rules as they are electrophile-driven, appear to proceed via a well-ordered chair-like transition state. The iodine can be replaced by hydroxy, acetoxy and azide groups.

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Article information

DOI
https://doi.org/10.1039/A902411E
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1999, 2143-2154

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Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols

S. B. Bedford, K. E. Bell, F. Bennett, C. J. Hayes, D. W. Knight and D. E. Shaw, J. Chem. Soc., Perkin Trans. 1, 1999, 2143 DOI: 10.1039/A902411E

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