1015-39-0Relevant academic research and scientific papers
Synthesis of chiral organotin reagents: Synthesis of enantiomerically enriched bicyclo[2.2.1]hept-2-yl tin hydrides from camphor. X-Ray crystal structures of (dimethyl)[(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]tin chloride and methyl(phenyl)bis[(
Helliwell, Madeleine,Thomas, Eric J.,Townsend, Linda A.
, p. 1286 - 1296 (2007/10/03)
2-Iodo-1,7,7-trimethylbicyclo[2.2.1]hept-2-ene 27 was prepared in two steps from camphor 23. Halogen-metal exchange using butyllithium followed by addition of the appropriate tin halide gave the corresponding bicyclo[2.2.1]-hept-2-en-2-ylstannanes 26, 35-
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 (2008/10/08)
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.
