N-烃基化和N-磺酰化的手性氨基醇和硼烷对前手性酮的不对称还原  

Asymmetric Reduction of Prochiral Ketones by Borane Catalyzed by N-Alkylated and N-Sulfonylated Chiral Aminoalcohol

作　　者：李春葆[1] 张健[1] 赵鹏英[1] 陆明[2] 

机构地区：[1]天津大学理学院,天津300072 [2]天津大学电子信息工程学院,天津300072

出　　处：《天津大学学报（自然科学与工程技术版）》2004年第10期923-925,共3页Journal of Tianjin University：Science and Technology

基　　金：天津大学青年教师基金资助项目(W50501).

摘　　要：为研究不对称催化合成反应,以L 亮氨酸为原料,由酯化、格式反应、还原N 烃基化反应合成3个新手性胺醇(6a,6b,6c),6b和6c经磺酰化得7a和7b.将手性配体6a,6b,6c,7a,7b分别与BH3·Me2S络合,由2种方法对芳香酮进行不对称还原,得芳香醇,不对称还原收率(ee)为3.9%～60.5%,其中手性磺胺醇的不对称催化收率较胺醇高.Asymmetric synthesis is becoming an even more interesting research area in chemistry.Aminoalcohols 6a, 6b and 6c were synthesized from L-leucine via esterification, Grignard reaction and reductive N-alkylation. Tosylation of 6b and 6c yielded 7a and 7b. After complexing with BH_3·Me_2S, 6a, 6b, 6c, 7a and 7b were tested in asymmetric reduction of aromatic ketones,to yield aromatic alcohols. The ee values ranged from (3.9%) to 60.5%. Tosylated ligands 7a and 7b gave better result than 6b and 6c.

关 键 词：不对称合成 N-烃基化 N-磺酰化 硼烷 胺基醇 

分 类 号：O621.254[理学—有机化学]