1611461-94-9Relevant academic research and scientific papers
Metal alkoxide promoted regio- and stereoselective Ci=O and Ci=C metathesis of allenoates with aldehydes
Wang, Minyan,Fang, Zhao,Fu, Chunling,Ma, Shengming
, p. 3214 - 3217 (2014)
The reaction of 2,3-allenoates and aldehydes in the presence of an alkoxide affords alkyl 4,5-diaryl-3-oxo-2-propylpent-4(E)-enoates and cis-3,4-diaryloxetanes through a formal Ci=O and Ci=C metathesis. A mechanism for this reaction has been proposed. All'ene' all: The reaction of aldehydes with 2,3-allenoates in the presence of tBuOM (M=Li or Na) affords the stereodefined, highly functionalized γ,δ-unsaturated β-ketoesters 1 in good to excellent yields with E stereoselectivity. The reactivity of 5-hydroxy-2,3-allenoates and the isolation of 3,4-diaryloxetanes led to a rationale for the mechanism of the reaction.
