Synthesis of 1-oxadecalins from anisole promoted by tungsten.
The complex TpW(NO)(PMe3)(eta(2)-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.
Lis
Edward C
EC
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA.
Salomon
Rebecca J
RJ
Sabat
Michal
M
Myers
William H
WH
Harman
W Dean
WD
D000171:Acrolein / Q000737:chemistry; D000840:Anisoles / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D014414:Tungsten / Q000737:chemistry*
D000840:Anisoles; D001643:Bridged Bicyclo Compounds; D009281:Naphthalenes; D009942:Organometallic Compounds; C449320:oxadecalin; D000171:Acrolein; C060998:anisole; D014414:Tungsten