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手性氨基醇(R)-2-氨基-1,1-二苯基-3-(2-萘基)-1-丙醇:制备及其对前手性酮硼烷还原的对映选择性催化作用
(R)-2-Amino-1,1-diphenyl-3-(2-naphthyl)-1-propanol:Preparation and Enantioselective Catalysis in the BoraneReduction of Prochiral Ketones
【摘要】 用丙二酸酯法合成了N-乙酰基-3-(2-萘基)-DL-α-丙氨酸乙酯3.3经酶法拆分,得光学活性的D-3,后者经盐酸水解、酯化后再与苯基溴化镁作用,制得标题化合物6。在0.5mmol6存在下,用过量硼烷对一系列前手性酮还原,得到了相应的光学活性二级醇。对映体过量(e.e值)57.0~100%。
【Abstract】 N-Acetyl-3-(2-naphthyl )-DL-α-alanine ethyl ester DL-3 was prepared via malonic ester method. The resolution of DL-3 with subtilisin earlsberg afforded D-3 , which, after converted to the corresponding amino acid methyl ester hydrochloride, reacted with phenyl magnesium bromide giving the title compound 6.In the presence of 6( 0.05 equiv.),prochiral ketones were reduced with excess borane yielding optically active secondary alcohols with e.e.57.6~100%.
【关键词】 手性氨基醇;
前手性酮;
对映选择性还原;
【Key words】 s: Chiral amino alcohol; Prochiral ketone; Enantioselective reduction.;
【Key words】 s: Chiral amino alcohol; Prochiral ketone; Enantioselective reduction.;
【基金】 国家自然科学基金
- 【文献出处】 合成化学 ,CHINESE JOURNAL OF SYNTHETIC CHEMISTRY , 编辑部邮箱 ,1996年04期
- 【分类号】O623.4
- 【被引频次】2
- 【下载频次】117