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

Research output: Contribution to journalArticle

2 Citations (Scopus)

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′.

Original languageEnglish
Pages (from-to)4811-4814
Number of pages4
JournalOrganic Letters
Volume20
Issue number16
DOIs
Publication statusPublished - Aug 17 2018

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4-Aminopyridine
Amides
amides
amino acids
Derivatives
Amino Acids
Kinetics
Benzoic Acid
benzoic acid
kinetics
products
4-N,N-dimethylaminopyridine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Dynamic Kinetic Resolution of Azlactones by a Chiral N, N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit : Importance of Amide Groups. / Mandai, Hiroki; Hongo, Kohei; Fujiwara, Takuma; Fujii, Kazuki; Mitsudo, Koichi; Suga, Seiji.

In: Organic Letters, Vol. 20, No. 16, 17.08.2018, p. 4811-4814.

Research output: Contribution to journalArticle

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