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

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

Research output: Contribution to journal › Article › peer-review

18 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 language	English
Pages (from-to)	4811-4814
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.8b01960
Publication status	Published - Aug 17 2018

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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′.",

author = "Hiroki Mandai and Kohei Hongo and Takuma Fujiwara and Kazuki Fujii and Koichi Mitsudo and Seiji Suga",

note = "Funding Information: This research was partially supported by a Grant-in-Aid for Young Scientists (B) (17K17903) from JSPS, a Grant-in-Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalysts,” and the JGC-S Scholarship Foundation. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b01960",

language = "English",

volume = "20",

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journal = "Organic Letters",

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T1 - Dynamic Kinetic Resolution of Azlactones by a Chiral N, N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit

T2 - Importance of Amide Groups

AU - Mandai, Hiroki

AU - Hongo, Kohei

AU - Fujiwara, Takuma

AU - Fujii, Kazuki

AU - Mitsudo, Koichi

AU - Suga, Seiji

N1 - Funding Information: This research was partially supported by a Grant-in-Aid for Young Scientists (B) (17K17903) from JSPS, a Grant-in-Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalysts,” and the JGC-S Scholarship Foundation. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/8/17

Y1 - 2018/8/17

N2 - 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′.

AB - 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′.

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DO - 10.1021/acs.orglett.8b01960

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SN - 1523-7060

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EP - 4814

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

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

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