A highly effective aldol reaction mediated by Ti(o-n-Bu)4/t-BuOK combined reagent

Tetrahedron Letters

Volumn 41, Issue 22, 2000, Pages 4415-4418

  Han, Zhenfu ^a   Yorimitsu, Hideki ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aldol reactions; Enals; Titanium and compounds

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BUTANEDIOL; REAGENT; TERT BUTYL ALCOHOL; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; STOICHIOMETRY; SYNTHESIS;

EID: 0034621998     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00642-0     Document Type: Article

References (23)

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20. 4) induced aldol condensation has been reported. See: Mahrwald, R.; Schick, H. Synthesis 1990, 592-594.
21. 4/LDA) afforded the aldol adduct in only 50% yield.
22. 4, concentrated in vacuo affording product 1 in 94% yield after silica-gel column purification.
23. The cross-aldol reaction between aldehyde and 2-alkynal could not give a satisfactory result under ordinary conditions because of the high reactivity of 2-alkynal and its aldol adduct. In fact, treatment of a mixture of heptanal and 2-octynal with t-BuOK alone in THF at 0°C provided a complex mixture. Thus, titanium alkoxide could play a critical role for the successful reaction.