Diastereofacial Control in the Reaction of Chiral α-Amino Ketones with Several Organometallics
作者:Tamotsu Fujisawa、Makoto Funabora、Yutaka Ukaji、Toshio Sato
DOI:10.1246/cl.1988.59
日期:1988.1.5
The addition reaction of organometallics to chiral α-amino ketones, prepared from α-halo ketones and (S)-2-methoxymethylpyrrolidine as a chiral auxiliary, gave different diastereomers of chiral amino alcohols depending on the difference of coordination ability of the metal used, i.e. organometallics such as Grignard reagent, organozinc, and cerium reagents preferred re-face attack, while organolithium
有机
金属化合物与手性α-
氨基
酮的加成反应,由α-卤代
酮和(S)-
2-甲氧基
甲基吡咯烷作为手性助剂制备,根据所用
金属的配位能力的差异,得到不同的手性
氨基醇的非对映异构体,即有机
金属化合物,如
格氏试剂、
有机锌和
铈试剂,更喜欢再表面攻击,而
有机锂化合物则从
硅表面攻击。