Chiral Transfer in the Reaction of Aminoallylic Stannanes with Carbonyls in Two Different Modes using Tin(II) and Indium(III) Halides for the Synthesis of Each Enantiomer

The
reaction of homochiral aminoallylic stannanes with aldehydes
gave carbonyl adducts of amino alcohols in the presence of either
SnCl2 or InBr3. Both additives afforded the
products in opposite absolute stereochemical configurations. The controlled
chirality was ascribed to the different transmetalation pathways of
SnCl2 and InBr3.

在氯化亚锡（SnCl₂）或三溴化铟（InBr₃）存在的条件下，同手性氨基烯丙基锡烷与醛发生反应，生成氨基醇的羰基加合物。两种添加剂均可得到该产物，但二者的绝对立体构型恰好相反。这种受控手性可归因于氯化亚锡与三溴化铟不同的转金属化反应路径。