Highly Enantioselective Pictet–Spengler Reactions with α-Ketoamide-Derived Ketimines: Access to an Unusual Class of Quaternary α-Amino Amides


  • This work was supported by a grant from the National Science Foundation (CHE-08-09659). F.R.B.-H. was supported by a postdoctoral fellowship from the MDS Research Foundation. We thank Prof. Ged Parkin and Aaron Sattler for an X-ray crystal structure analysis (see the Supporting Information), and the National Science Foundation (CHE-0619638) is thanked for acquisition of an X-ray diffractometer.


Quat's” the story?N-Aryl amides are effective directing/activating groups for chlorosilane Lewis acids. This aspect has been exploited for the development of the first simple and general method for the highly enantioselective Pictet–Spengler reaction of ketimines derived from α-ketoamides leading to quaternary α-amino acid derivatives (see scheme).

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