title: Bifunctional amino sulfonohydrazide catalyzed direct asymmetric Mannich reaction of cyclic ketimines with ketones: highly diastereo- and enantioselective construction of quaternary carbon stereocenters.
abstract: A bifunctional amino sulfonohydrazide which contains multiple sites for hydrogen bonding with substrates was found to enhance reactivity and enantioselectivity in the direct asymmetric Mannich reaction of N-sulfonyl cyclic ketimines with ketones. In this efficient transformation, not only methyl ketones but also cyclic ketones can be employed to provide a general methodology to construct tetrasubstituted α-amino ester in a stereoselective manner. The synthetic utility of a substituted amino ester product is demonstrated by the synthesis of biologically active spirotetrahydrofuran.
authors: Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry & Collaborative Innovation Center of Suzhou Nano Science and Technology, Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, P. R. China.
authors: Sheng
authors: S
authors: Zhang
authors: Lijun
authors: L
authors: Li
authors: Yanbin
authors: Y
authors: Hu
authors: Zhenggen
authors: Z
authors: Zha
authors: Zhiyong
authors: Z
authors: Wang
authors: Teck-Peng
authors: TP
authors: Loh
mesh_terms: D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D007649:Ketamine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D004952:Esters; D007659:Ketones; D013450:Sulfones; D007649:Ketamine; D002244:Carbon