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手性二茂铁基β-氨基醇的合成及其在醛酮对映选择性反应中的应用
Synthesis of Chiral Ferrocenyl β-Amino Alcohols and Catalytic Application in Enantioselective Reaction of Aldehyde and Ketone
【摘要】 从二茂铁和廉价易得的L-缬氨酸、苯丙氨酸出发,合成了4个手性氨基醇衍生的二茂铁基β-氨基醇.研究了它们对醛的不对称加成和前手性酮不对称氢转移反应的对映选择性.特别在钌催化的苯乙酮的不对称氢转移反应中,二茂铁基氨基醇4b以最好99.1%的产率和74.2%e.e.值,得到产物R-1-苯-1-乙醇.而用与4b对应的α-胺基膦氧化物5催化时,化学产率和e.e.值分别为51.5%和41.1%.
【Abstract】 Four chiral ferrocenyl β-amino alcohols ligands were synthesized in high yields Staring from ferrocene and natural L-amino acids under mild conditions.These chiral ligands were further applied in the asymmetric addition of diethylzinc to aldehyde and asymmetric transfer hydrogenation of acetophenone.In ruthenium-catalyzed asymmetric transfer hydrogenation reactions,the best result was given by 4b,and the corresponding(R)-1-phenyl-1-ethanol was isolated in 99.1% yield with 74.2% e.e.The α-ferrocenyl-α-aminophosphine oxide 5 gave(R)-1-phenyl-1-ethanol in 51.5% yield with 41.1% e.e.
【Key words】 chiral ferrocenyl β-amino alcohols; asymmetric addition of aldehyde; asymmetric transfer hydrogenation of acetophenone;
- 【文献出处】 山西师范大学学报(自然科学版) ,Journal of Shanxi Normal University(Natural Science Edition) , 编辑部邮箱 ,2008年03期
- 【分类号】O627.81
- 【被引频次】1
- 【下载频次】134