Titanium Binolate Catalyzed Aminolysis of meso Aziridines: A Highly Enantioselective and Direct Access to 1,2-Diamines

被引:46
|
作者
Peruncheralathan, Saravanan [1 ]
Teller, Henrik [1 ]
Schneider, Christoph [1 ]
机构
[1] Univ Leipzig, Inst Organ Chem, D-4103 Leipzig, Germany
关键词
asymmetric catalysis; aziridines; desymmetrization; 1,2-diamines; titanium; GLYOXYLATE ENE REACTION; ALPHA-HYDROXY ESTERS; ASYMMETRIC ALLYLATION; PRACTICAL ACCESS; ALKYL-GROUPS; ALDEHYDES; DESYMMETRIZATION; COMPLEXES; DIETHYLZINC; MECHANISM;
D O I
10.1002/anie.200901110
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
It's as simple as that: An in situ prepared chiral catalyst from the commercially available compounds Ti(OiPr)4 and (R)-binol catalyzes the highly enantioselective ring-opening of meso-aziridines 1 with anilines 2 and furnishes valuable chiral 1,2-diamines 3 in high yields and up to 99 % ee.(R)- binol=(R)-2,2′-dihydroxy-1,1′-binaphthyl. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4849 / 4852
页数:4
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