Journal of Organic Chemistry p. 2239 - 2244 (1987)
Update date:2022-08-05
Topics:
Nakano Tatsuya
Irifune Shinji
Umano Shigetoshi
Inada Akihiro
Ishii Yasutaka
Ogawa Masaya
Under the influence of zirconocene complex,Cp2ZrH2 (1) or Cp2Zr(O-i-Pr)2 (9),cycloalkanones 2 condensed directly with aliphatic aldehydes 3 or primary alcohols 7 to form 2-alkylidenecycloalkanones 4 or 2-alkyl-2-cycloalken-1-ones 8,respectively,in fair to substantial yields.The selectivity of the cross-condensations was slighty improved by using 1 in combination with a metal salt such as NiCl2.Dihydrojasmone (13) was synthesized in 35percent yield by one-step reaction from the commercially available 3-methylpentanone (2e) with pentanol (7b) in the presence of 1 and NiCl2.
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