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Synlett 2004(1): 65-68
DOI: 10.1055/s-2003-43378
DOI: 10.1055/s-2003-43378
LETTER
© Georg Thieme Verlag Stuttgart · New YorkPolarity Controlled Reversal of 5-Exo/6-endo-Selectivities in the Synthesis of β-Brominated Cyclic Ethers
Further Information
Received
24 October 2003
Publication Date:
04 December 2003 (online)
Publication History
Publication Date:
04 December 2003 (online)

Abstract
Polar bromocyclizations of bishomoallylic alcohols (nucleophilic oxygen), which have methyl and/or phenyl substituents located at positions 1, 4, and/or 5, and cyclizations of the derived alkenoxyl radicals (electrophilic oxygen) followed by bromine atom trapping from BrCCl3, proceed with complementary regioselectivities.
Key words
alkoxyl radical - bromide oxidation - tert-butyl hydroperoxide - Mitsunobu reaction - vanadium
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