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Synfacts 2006(10): 0997-0997
DOI: 10.1055/s-2006-949343
DOI: 10.1055/s-2006-949343
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
α-Difluoromethylenephostones by Iodocyclization
Y. Lin, J.-T. Liu*
Shanghai Institute of Organic Chemistry, P. R. of China
Further Information
Publication History
Publication Date:
21 September 2006 (online)
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Significance
The synthesis of a biological relevant class of cyclic α-difluoromethylenephosphonates (phostones) utilizing a mild and regioselective iodocyclization of β-allenic phosphonates in moderate to high yields is reported. The starting β-allenic phosphonates are readily prepared from propargylic tosylates. A mechanism involving iodine-initiated, thermodynamically favored endo cyclization is proposed. Relative facility of the reaction may be rationalized on the basis of stability and steric factors involved in the formation of the iodonium intermediate.