Novel Knöevenagel-type reaction via titanium enolate derived from Ti(O-i-Pr)4 and diketene

Tetrahedron

Volumn 60, Issue 32, 2004, Pages 6777-6783

  Hayashi, Masahiko ^a   Nakamura, Norihiro ^a   Yamashita, Kohei ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

Diketene; Kn evenagel reaction; Titanium enolate

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALDEHYDE; ISOPROPYL 2 ACETYL 3 PHENYL 2 PROPENOATE; KETENE DERIVATIVE; TITANIUM DERIVATIVE; TITANIUM ENOLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; ISOMER; KNOEVENAGEL CONDENSATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TANDEM MASS SPECTROMETRY;

EID: 3142717331     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.018     Document Type: Article

References (14)

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12. Reaction of diketene with benzaldehyde in the presence of sulfuric acid was reported, see: Kato T., Chiba T., Sato M. Chem. Pharm. Bull. 26:1987;3877-3879
13. Conventional Knöevenagel reaction of methyl acetoacetate with aldehydes catalyzed by piperidine was studied by Tanikaga and his co-workers, see: Tanikaga R., Konya N., Hamamura K., Kaji A. Bull. Chem. Soc. Jpn. 61:1988;3211-3216
14. From the E-isomer (100%) it took 6 h at 90 °C to reach thermodynamic ratio (E/Z=33/67) (at room temperature it took more than 2 weeks). On the other hand, from the Z-isomer it took 18 h to reach thermodynamic ratio (E/Z=33/67) at the same temperature