1129-51-7Relevant academic research and scientific papers
The magnesium-ene cyclization stereochemically directed by an allylic oxyanionic group and its application to a highly stereoselective synthesis of (±)-matatabiether. Allylmagnesium compounds by reductive magnesiation of allyl phenyl sulfides
Cheng,Zhu,Yu,Cohen
, p. 30 - 34 (2007/10/03)
The first example of a magnesium-ene cyclization stereochemically directed by an allylic oxyanionic group is demonstrated by a highly stereoselective synthesis of the bicyclic terpene matatabiether 10. The synthetic method is particularly valuable, not only because of the stereochemical control and the utility of the versatile hydroxyl group introduced into the product, but also because the precursor of the allylmagnesium is an allyl phenyl sulfide, which is more stable and more easily prepared in a connective fashion than the usual allyl halide precursor. Since the presence of lithium ions encourages undesirable proton transfer to the cyclized organometallic and is detrimental to the stereochemical control, the conversion of the allylic thioether to the allylmagnesium utilizes a lithium-free method involving direct reductive magnesiation in the presence of the magnesium-anthracene complex.
Selective Condensation of titanium Reagent with Carbonyl Compounds
Furuta, Kyoji,Ikeda, Yoshihiko,Meguriya, Noriyuki,Ikeda, Nobuo,Yamamoto, Hisashi
, p. 2781 - 2790 (2007/10/02)
titanium reagent generated easily from allyl ethyl sulfides condensed with aldehydes to give erythro-β-hydroxy sulfides in highly regio- and stereoselective manner.In contrast, crotyl ethyl sulfide reacted with aldehydes affording δ-hydroxy vinyl sulfide exclusively.The substitution pattern of the starting sulfide can have a pronounced effect on the selectivity in this condensation reaction, erythro-β-Hydroxy sulfide obtained was transfromed stereoselectively to the trans-vinyloxirane or 1,3-alkadiene.
