96206-35-8Relevant academic research and scientific papers
Enantioselective syntheses of (E)-γ,δ-disubstituted homoallylic alcohols via BF3·OEt2-catalyzed aldehyde allylboration and analysis of the origin of E-selectivity: A1,2 allylic strain vs. syn-pentane interaction
Liu, Jiaming,Gao, Shang,Chen, Ming
, p. 4110 - 4117 (2019)
Enantioselective allylboration of aldehydes with α-substituted β-methyl allylboronate was reported. By using BF3·OEt2 as the catalyst, γ,δ-disubstituted homoallylic alcohols were obtained in good yields with high E-selectivities and
Highly selective allylborations of aldehydes using α,α- disubstituted allylic pinacol boronic esters
Hesse, Matthew J.,Essafi, Stephanie,Watson, Charlotte G.,Harvey, Jeremy N.,Hirst, David,Willis, Christine L.,Aggarwal, Varinder K.
, p. 6145 - 6149 (2014/06/23)
α,α-Disubstituted allylic pinacol boronic esters undergo highly selective allylborations of aldehydes to give tetrasubstituted homoallylic alcohols with exceptional levels of anti-Z-selectivity (>20:1). The scope of the reaction includes both acyclic and
Z-Selective Synthesis of Homoallylic Alcohols via 2-Alkenylation of Aldehydes by 1-(Tributylstannyl)-2-alkene
Miyake, Hideyoshi,Yamamura, Kimiaki
, p. 897 - 900 (2007/10/02)
1-(Tributylstannyl)-2-alkene reacts with a solution of an aldehyde and BuSnCl3 to give (Z)-homoallylic alcohol.Z-Selective 2-methyl-2-butenylation can be accomplished by using (Z)-2-methyl-1-(tributylstannyl)-2-butene instead of 1-(tributylstannyl)-2-alkene.This reaction is useful as a new method to make (Z)-double bond.An application ot the present method for a synthesis of pheromones is also described.
