Tetrahedron p. 435 - 450 (1985)
Update date:2022-08-05
Topics: Oxidation Regioselectivity Kinetic studies Reduction Chromatography Retro-aldol reaction Nucleophilic Attack Stereoselectivity Ring Expansion Spectroscopic Analysis Thermodynamic Control Tautomerization Electrophilic addition Ring contraction Acid-catalyzed rearrangement 1,2-hydride shift
novak
Szantay
Meisel
Aszodi
Szabo
fekete
Novel rearrangements of hydroxycyclopentenone derivatives 1 and 24 to 7,9,11 and 31,33,35 are reported. The stereochemistry of the rearrangement is interpreted as the result of synchronous enolate induced [1.5]-sigmatropic rearrangement and stepwise addition-elimination process. Preparation of the various substrates and structural elucidation of new products are also described.
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(1985)
