Asymmetric direct amide synthesis by kinetic amine resolution:: A chiral bifunctional aminoboronic acid catalyzed reaction between a racemic amine and an achiral carboxylic acid

被引:158
作者
Arnold, Kenny [1 ]
Davies, Bryan [2 ]
Herault, Damien [1 ]
Whiting, Andrew [1 ]
机构
[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3QZ, England
[2] GlaxoSmithKline, Discovery Res Syst Chem, Stevenage SG1 2NY, Herts, England
关键词
boronates; homogeneous catalysis; kinetic resolution; selectivity;
D O I
10.1002/anie.200705643
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Let's resolve this: A planar chiral benzimidazole ferroceneboronic acid catalyst demonstrates low to moderate asymmetric induction in the kinetic resolution of racemic α-substituted benzylamines by direct amide formation with achiral carboxylic acids (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2673 / 2676
页数:4
相关论文
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[31]   Convenient preparation of chiral phase-transfer catalysts with conformationally fixed biphenyl core for catalytic asymmetric synthesis of α-alkyl- and α,α-dialkyl-α-amino acids:: application to the short asymmetric synthesis of BIRT-377 [J].
Wang, Yong-Gang ;
Ueda, Mitsuhiro ;
Wang, Xisheng ;
Han, Zhenfu ;
Maruoka, Keiji .
TETRAHEDRON, 2007, 63 (26) :6042-6050