Chiral Sulfoxides as Neutral Coordinate-Organocatalysts in Asymmetric Allylation of <i>N</i>-Acylhydrazones Using Allyltrichlorosilanes
作者:Shū Kobayashi、Chikako Ogawa、Hideyuki Konishi、Masaharu Sugiura
DOI:10.1021/ja035061m
日期:2003.6.1
Sulfoxides were first introduced to the allylation of N-acylhydrazones with allyltrichlorosilanes as effective neutral coordinate-organocatalysts (NCOs). Both high diastereo- and enantioselectivity were attained when optically active chiral sulfoxides were used. Asymmetric crotylations using (Z)- and (E)-crotyltrichlorosilanes showed a high level of stereospecificity (Z --> anti and E --> syn) with
亚砜首先被引入到 N-酰基腙与烯丙基三氯硅烷的烯丙基化反应中,作为有效的中性配位有机催化剂 (NCO)。当使用旋光手性亚砜时,可以获得高的非对映选择性和对映选择性。使用 (Z)- 和 (E)-巴豆基三氯硅烷的不对称巴豆化显示出高水平的立体特异性(Z --> anti 和 E --> syn),具有高对映选择性。