Control of diastereoselectivity in the crotylation and cinnamylation of aldehydes by the selection of ligands on allylic indium reagents.
Diastereoselective couplings of salicylaldehyde, anisaldehyde and 2-pyridylaldehyde with crotyl- and cinnamylindium reagents were studied. The syl/anti selectivity was found to depend largely on the ligands on the indium atom of the allylic indium reagents. A syn-selective cinnamylation of salicylaldehyde was realized by the combination of cinnamyl acetate and indium(I) iodide, whereas an anti-selective coupling with salicylaldehyde was achieved by the indium trichloride/aluminium-mediated cinnamylation.
Hirashita
Tsunehisa
T
Omohi College, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan. hirasita@ach.nitech.ac.jp
Kamei
Toshiya
T
Satake
Makoto
M
Horie
Tomoaki
T
Shimizu
Hidetaka
H
Araki
Shuki
S