1095180-03-2Relevant academic research and scientific papers
Controllable highly stereoselective reaction of in situ generated magnesium dienolate intermediates with different electrophiles
Lu, Zhan,Chai, Guobi,Zhang, Xiaobing,Ma, Shengming
supporting information; experimental part, p. 3517 - 3520 (2009/05/07)
(Chemical Equation Presented) In this paper, we have described an efficient controllable stereoselective a-acylation and -allylation reaction of the magnesium dienolate intermediates generated in situ from the Fe(lll)-catalyzed reaction between 2,3-allenoates and Grignard reagents with different electrophiles to afford 2-acylated or allylated 3(Z)- or (E)-alkenoates depending on the nature of the electrophiles and reaction conditions. The distinct stereoselectivity may be caused by the isomerization of metallic Z-1,3-dienoate to E-1,3-dienoate via the intermediacy of anti-allylic MgCl and syn-metallic species.
