96292-71-6Relevant academic research and scientific papers
Synthesis of optically active allyltin compounds and their application to enantioselective synthesis of secondary homoallyl alcohols
Otera, Junzo,Yoshinaga, Yukari,Yamaji, Takeshi,Yoshioka, Takakazu,Kawasaki, Yuzuru
, p. 1213 - 1218 (1985)
Three types of optically active allyltin compounds, R*2Sn(allyl)2 (R* = 2-phenylbutyl, 2-methylbutyl, and 3-phenylbutyl), R*R1Sn(allyl)2 (R* = 2-octyl or 2-phenylbutyl, R1 = phenyl), and R*R1R2Sn(allyl) (R* = 2-phenylbutyl, R1 = phenyl, R2 = methyl), have been synthesized. On the basis of 1H NMR spectra, a π-stacking interaction between the 2-phenylbutyl and the allyl groups is suggested. Optically active allyltin compounds thus obtained were subjected to reaction with aldehydes. Among various allyltin compounds, only diallylbis(2-phenylbutyl)tin exhibits good enantioselectivity. The reaction proceeds through addition of the allyl group on the re face of aldehydes. The mechanism can be accounted for on the basis of a π-stacking interaction between allyl and phenyl groups.
