Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester-Amide Exchange Reaction

Ryota Nakao; Yudai Fujii; Ichiro Hayakawa; Haruki Mizoguchi; Akira Sakakura

doi:10.1055/s-0040-1707303

Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester-Amide Exchange Reaction

Ryota Nakao, Yudai Fujii, Ichiro Hayakawa, Haruki Mizoguchi, Akira Sakakura

School of Engineering

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

3 Citations (Scopus)

Abstract

C1 -Symmetric chiral ammonium salt catalysts induced a kinetic resolution of racemic α-nitrolactones through an asymmetric ester-amide exchange reaction. The corresponding amides were obtained with high enantioselectivities and high S (= k fast / k slow) values. This reaction system is a useful approach for obtaining carbocyclic quaternary α-nitroamides as chiral building blocks.

Original language	English
Pages (from-to)	2018-2022
Number of pages	5
Journal	Synlett
Volume	31
Issue number	20
DOIs	https://doi.org/10.1055/s-0040-1707303
Publication status	Published - Dec 17 2020

Keywords

Bronsted acid catalysis
ester-amide exchange
hydrolysis
kinetic resolution
nitrolactones
quaternary amino acids

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0040-1707303

Cite this

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title = "Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester-Amide Exchange Reaction",

abstract = "C1 -Symmetric chiral ammonium salt catalysts induced a kinetic resolution of racemic α-nitrolactones through an asymmetric ester-amide exchange reaction. The corresponding amides were obtained with high enantioselectivities and high S (= k fast / k slow) values. This reaction system is a useful approach for obtaining carbocyclic quaternary α-nitroamides as chiral building blocks. ",

keywords = "Bronsted acid catalysis, ester-amide exchange, hydrolysis, kinetic resolution, nitrolactones, quaternary amino acids",

author = "Ryota Nakao and Yudai Fujii and Ichiro Hayakawa and Haruki Mizoguchi and Akira Sakakura",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research (C) (No. 15K05123) from MEXT, the Naito Foundation, and the Okayama Foundation for Science and Technology.OkayamaFoundaionforScienceandTechnology(NaitoFoundatonMinitsyofEducaion, Culute, Spos, ScienceandTechnology(15K05123) Publisher Copyright: {\textcopyright} 2020. Thieme. All rights reserved.",

year = "2020",

month = dec,

day = "17",

doi = "10.1055/s-0040-1707303",

language = "English",

volume = "31",

pages = "2018--2022",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "20",

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TY - JOUR

T1 - Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester-Amide Exchange Reaction

AU - Nakao, Ryota

AU - Fujii, Yudai

AU - Hayakawa, Ichiro

AU - Mizoguchi, Haruki

AU - Sakakura, Akira

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research (C) (No. 15K05123) from MEXT, the Naito Foundation, and the Okayama Foundation for Science and Technology.OkayamaFoundaionforScienceandTechnology(NaitoFoundatonMinitsyofEducaion, Culute, Spos, ScienceandTechnology(15K05123) Publisher Copyright: © 2020. Thieme. All rights reserved.

PY - 2020/12/17

Y1 - 2020/12/17

N2 - C1 -Symmetric chiral ammonium salt catalysts induced a kinetic resolution of racemic α-nitrolactones through an asymmetric ester-amide exchange reaction. The corresponding amides were obtained with high enantioselectivities and high S (= k fast / k slow) values. This reaction system is a useful approach for obtaining carbocyclic quaternary α-nitroamides as chiral building blocks.

AB - C1 -Symmetric chiral ammonium salt catalysts induced a kinetic resolution of racemic α-nitrolactones through an asymmetric ester-amide exchange reaction. The corresponding amides were obtained with high enantioselectivities and high S (= k fast / k slow) values. This reaction system is a useful approach for obtaining carbocyclic quaternary α-nitroamides as chiral building blocks.

KW - Bronsted acid catalysis

KW - ester-amide exchange

KW - hydrolysis

KW - kinetic resolution

KW - nitrolactones

KW - quaternary amino acids

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U2 - 10.1055/s-0040-1707303

DO - 10.1055/s-0040-1707303

M3 - Article

AN - SCOPUS:85092742982

SN - 0936-5214

VL - 31

SP - 2018

EP - 2022

JO - Synlett

JF - Synlett

IS - 20

ER -

Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester-Amide Exchange Reaction

Abstract

Keywords

ASJC Scopus subject areas

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