Synthesis of 1-Oxadecalins from Anisole Promoted by Tungsten

The complex TpW(NO)(PMe3)(η2-anisole) is combined with acrolein or methyl vinyl ketone and various nucleophiles to generate novel chromen complexes. These complexes may be further elaborated by protonation and nucleophilic addition to generate chroman analogues with increased saturation and stereoce...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-09, Vol.130 (37), p.12472-12476
Main Authors: Lis, Edward C, Salomon, Rebecca J, Sabat, Michal, Myers, William H, Harman, W. Dean
Format: Article
Language:English
Subjects:
Acrolein - chemistry
Anisoles - chemistry
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Naphthalenes - chemical synthesis
Naphthalenes - chemistry
Organometallic Compounds - chemistry
Tungsten - chemistry
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Summary:The complex TpW(NO)(PMe3)(η2-anisole) is combined with acrolein or methyl vinyl ketone and various nucleophiles to generate novel chromen complexes. These complexes may be further elaborated by protonation and nucleophilic addition to generate chroman analogues with increased saturation and stereocenters. Treatment with various oxidants effects the decomplexation of the chromen.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja803605m