283166-69-8Relevant academic research and scientific papers
Convenient methods for the preparation of unsymmetrical double aldols
Mukaiyama, Teruaki,Pudhom, Khanitha,Yamane, Keiko,Arai, Hidehiro
, p. 413 - 425 (2007/10/03)
Double aldol reaction proceeded stereoselectively at one α-carbon of ketones to give α-(1-hydroxyalkyl)-β-hydroxyalkyl ketones (double aldols) in good to high yields by the following three methods: i) tin(II) trifluoromethanesulfonate-mediated aldol reaction of aldehydes with β-hydroxy ketones (mono-aldols) in the presence of tertiary amines, ii) samarium(II) iodide-mediated aldol reaction of aldehydes with alkyl or aryl oxiranyl ketones, iii) Sn(OTf)2- promoted aldol reaction of α-bromo ketones with aldehydes giving α-bromo-β-stannyloxy ketones which were then converted to titanium enolates on treatment with low-valent titanium. Double aldols were formed by subsequent reaction of the above titanium enolates with aldehydes in one-pot procedure. Further, small and medium-sized carbocyclic compounds whose ring skeletons were composed of double aldol structure were synthesized by SmI2-mediated intramolecular cyclization between oxiranyl ketone and aldehyde functions.
A new method for the synthesis of unsymmetrical bis-aldols by the samarium(II) iodide-mediated aldol reaction of aldehydes with aryl or alkyl oxiranyl ketones
Mukaiyama, Teruaki,Arai, Hidehiro,Shiina, Isamu
, p. 580 - 581 (2007/10/03)
Unsymmetrieal alkyl or aryl 2-hydroxy-1-(1-hydroxyalkyl)-alkyl ketones (bis-aldols) were synthesized by the samarium(II) iodide-mediated aldol reaction of aldehydes with alkyl or aryl oxiranyl ketones. Bis-aldols were formed via the aldol reaction of aldehydes with samarium enolates generated by epoxy-fragmentation of oxiranyl ketones using two moles of samarium(II) iodide.
