Dynamic Kinetic Resolution of Azlactones by a Chiral N, N-Dimethyl-4-aminopyridine Derivative Containing a 1,1'-Binaphthyl Unit: Importance of Amide Groups

Hiroki Mandai; Kohei Hongo; Takuma Fujiwara; Kazuki Fujii; Koichi Mitsudo; Seiji Suga

doi:10.1021/acs.orglett.8b01960

Dynamic Kinetic Resolution of Azlactones by a Chiral N, N-Dimethyl-4-aminopyridine Derivative Containing a 1,1'-Binaphthyl Unit: Importance of Amide Groups

Org Lett. 2018 Aug 17;20(16):4811-4814. doi: 10.1021/acs.orglett.8b01960. Epub 2018 Jul 26.

Authors

Hiroki Mandai¹, Kohei Hongo¹, Takuma Fujiwara¹, Kazuki Fujii¹, Koichi Mitsudo¹, Seiji Suga¹

Affiliation

¹ Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushima-naka , Kita-ku, Okayama 700-8530 , Japan.

PMID: 30048141
DOI: 10.1021/acs.orglett.8b01960

Abstract

A dynamic kinetic resolution (DKR) of azlactones in the presence of benzoic acid and a binaphthyl-based N, N-4-dimethylaminopyridine (DMAP) derivative 1i having two amide groups at the 3,3'-positions of a binaphthyl unit is developed. The reaction proceeded smoothly with a wide range of azlactones to provide α-amino acid derivatives with good to high enantiomeric ratios (er's). A multigram-scale reaction (2.5 g) for the DKR of azlactone 2d was also demonstrated, and the resulting product was converted to unnatural α-amino acid 6d'.

Publication types

Research Support, Non-U.S. Gov't