Free accessResearch articleFirst published online 2004-9
Crystal structure of 4-benzyloxy- and 4-hydroxy– ( Z )-3-[(6-bromo-1,3-benzodioxol-5-yl)methylene]-2-(4-methoxybenzyl)-2,3-dihydro-1 H -isoindol-1-ones
In contrast to unsubstituted models, the Horner reaction between phosphorylated 4-benzyloxyisoindolinone and ortho-bromobenzaldehyde gives rise selectively to the arylmethylene derivative with a Z-configuration.
RobinM.B., BoveyF. A., and BaschH., Molecular and Electronic Structure of the Amide Group, in The Chemistry of Amides, eds PataiS., and ZabickyJ., John Wiley & Sons, London, 1970, pp. 1–72.
2.
ChangZ.-L., and ZhuD.-Y., in The Alkaloids, eds BrossiA., Academic Press, New York, 1978, Vol. 31, pp. 29–65.
3.
CoutureA., DeniauE., GrandclaudonP., and HoarauC., J. Org. Chem., 1998, 63, 3128.
4.
CoutureA., DeniauE., GrandclaudonP., and HoarauC., Tetrahedron, 2000, 56, 1491–1499.
5.
HoarauC., CoutureA., CornetH., DeniauE., and GrandclaudonP., J. Org. Chem., 2001, 66, 8064–8069.
6.
TojoE., DominguezD., and CastedoL., Phytochemistry, 1991, 30, 1005–1010.
7.
MoreauA., CoutureA., DeniauE., and GrandclaudonP., J. Org. Chem., 2004, 69, 4527–4530.
8.
SheldrickG.M., SHELXTL, Program for Crystal Structure Solution and Refinement, Bruker AXS Inc., Madison, WI, 1997.
