Oxidative Kinetic Resolution of Acyclic Amines Based on Equilibrium Control

Kodai Saito; Hiromitsu Miyashita; Yui Ito; Masahiro Yamanaka; Takahiko Akiyama

doi:10.1021/acs.orglett.0c00887

Oxidative Kinetic Resolution of Acyclic Amines Based on Equilibrium Control

Kodai Saito, Hiromitsu Miyashita, Yui Ito, Masahiro Yamanaka, Takahiko Akiyama

Department of Chemistry

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

1 Citation (Scopus)

Abstract

An oxidative kinetic resolution of racemic acyclic amines was developed using an imine derivative as the resolving reagent and chiral phosphoric acid as the catalyst to give enantiomers in good yields with high to excellent enantioselectivities. The key to success of the title reaction was the equilibrium control by adjusting the ratio of the resolving reagent, and unique enantiodivergence was observed depending on the equilibrium displacement.

Original language	English
Pages (from-to)	3128-3134
Number of pages	7
Journal	Organic Letters
Volume	22
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.0c00887
Publication status	Published - 2020 Apr 17

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c00887

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title = "Oxidative Kinetic Resolution of Acyclic Amines Based on Equilibrium Control",

abstract = "An oxidative kinetic resolution of racemic acyclic amines was developed using an imine derivative as the resolving reagent and chiral phosphoric acid as the catalyst to give enantiomers in good yields with high to excellent enantioselectivities. The key to success of the title reaction was the equilibrium control by adjusting the ratio of the resolving reagent, and unique enantiodivergence was observed depending on the equilibrium displacement.",

author = "Kodai Saito and Hiromitsu Miyashita and Yui Ito and Masahiro Yamanaka and Takahiko Akiyama",

note = "Funding Information: This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Advanced Transformation Organocatalysis” from MEXT, Japan, JSPS KAKENHI (17H03060 for T.A. and 17KT0011 for M.Y.), and the MEXT-supported Program for the Strategic Research Foundation at Private Universities. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

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AU - Akiyama, Takahiko

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N2 - An oxidative kinetic resolution of racemic acyclic amines was developed using an imine derivative as the resolving reagent and chiral phosphoric acid as the catalyst to give enantiomers in good yields with high to excellent enantioselectivities. The key to success of the title reaction was the equilibrium control by adjusting the ratio of the resolving reagent, and unique enantiodivergence was observed depending on the equilibrium displacement.

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Oxidative Kinetic Resolution of Acyclic Amines Based on Equilibrium Control

Abstract

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