イミン類のアリル化およびプロパルギル化反応：位置選択性に与える水の影響

抄録

Allylation and propargylation reactions of imine derivatives in the presence of a catalytic amount of palladium complex and indium(I) iodide were studied. The reversibility of allylation was observed in the reaction of glyoxylic oxime ether having camphorsultam. Excellent diastereoselectivity in allylation of glyoxylic oxime ether with allyl acetate was achieved in the presence of water, although low diastereoselectivity was observed in the absence of water. In the presence of water, the γ-adducts were kinetically formed from monosubstituted allylic reagents. In contrast, the selective formation of thermodynamically stable α-adducts was observed in anhydrous THF. Propargylation of glyoxylic oxime ether proceeded with good diastereoselectivities in the presence of Pd(dppf)Cl₂ and LiCl.

Scheme 1