29337-79-9Relevant academic research and scientific papers
On the stereochemistry of the olefinic double bond in 13-membered heterocyclic rings accessible by ring-closing metathesis reaction
Rao, H. Surya Prakash,Rafi, Shaik,Ratish Kumar,Guravaiah,Muthanna, Nandurka
, p. 6877 - 6880 (2013/01/15)
13-Membered heterocyclic ring analogs of the core structure of manzamine alkaloids were synthesized by ring closing metathesis (RCM) reaction. The influence of a remote heteroatom (N, O, S) on E/Z stereochemistry of the olefinic double bond formed in RCM reaction using Grubbs 1st and 2nd generation ruthenium carbene complexes was evaluated. Studies show that RCM reaction is kinetically controlled and the hetero atoms influence the double bond stereochemistry.
Reduction of flavanones by NaBH3CN in trifluoroacetic acid.
Lewin, G.,Bert, M.,Dauguet, J. C.,Dolley, J.,Menez, P. Le,et al.
, p. 939 - 944 (2007/10/02)
For our studies on the reduction of flavanones, we worked on flavanone itself and on some other derivatives, oxygenated on the B ring.Besides expected flavans and chalcanes, condensed compounds (dimers and trimers) are also obtained.Reaction begins with the reduction of carbonyl to methylene; all the other isolated products arise from the two possible and competitive reactions on the potential carbocation C-2 of the flavan system: a) reductive cleavage of heterocycle; b) electrophilic aromatic substitution.Reactivity of flavanones is correlated with substituents of B ring through their ?+ values. Key words: flavanones / sodium cyanoborhydride / trifluoroacetic acid / flavans / chalcanes / dimers
