Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

Yoshito Takahashi; Risa Yoshii; Takaaki Sato; Noritaka Chida

doi:10.1021/acs.orglett.8b02421

Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

Yoshito Takahashi, Risa Yoshii, Takaaki Sato, Noritaka Chida

Department of Applied Chemistry

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

20 Citations (Scopus)

Abstract

An iridium-catalyzed reductive nucleophilic addition to secondary amides is reported. After the iridium-catalyzed reduction, the resulting imines can undergo the Strecker reaction, the Mannich reaction, allylation, and [3 + 2]-cycloaddition. The method shows high chemoselectivity in the presence of other functional groups such as methyl ester.

Original language	English
Pages (from-to)	5705-5708
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.8b02421
Publication status	Published - 2018 Sep 21

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides",

abstract = "An iridium-catalyzed reductive nucleophilic addition to secondary amides is reported. After the iridium-catalyzed reduction, the resulting imines can undergo the Strecker reaction, the Mannich reaction, allylation, and [3 + 2]-cycloaddition. The method shows high chemoselectivity in the presence of other functional groups such as methyl ester.",

author = "Yoshito Takahashi and Risa Yoshii and Takaaki Sato and Noritaka Chida",

note = "Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (C) from MEXT (18K05127) and the Tobe Maki Foundation.",

year = "2018",

month = sep,

day = "21",

doi = "10.1021/acs.orglett.8b02421",

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journal = "Organic Letters",

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T1 - Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

AU - Takahashi, Yoshito

AU - Yoshii, Risa

AU - Sato, Takaaki

AU - Chida, Noritaka

N1 - Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (C) from MEXT (18K05127) and the Tobe Maki Foundation.

PY - 2018/9/21

Y1 - 2018/9/21

N2 - An iridium-catalyzed reductive nucleophilic addition to secondary amides is reported. After the iridium-catalyzed reduction, the resulting imines can undergo the Strecker reaction, the Mannich reaction, allylation, and [3 + 2]-cycloaddition. The method shows high chemoselectivity in the presence of other functional groups such as methyl ester.

AB - An iridium-catalyzed reductive nucleophilic addition to secondary amides is reported. After the iridium-catalyzed reduction, the resulting imines can undergo the Strecker reaction, the Mannich reaction, allylation, and [3 + 2]-cycloaddition. The method shows high chemoselectivity in the presence of other functional groups such as methyl ester.

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U2 - 10.1021/acs.orglett.8b02421

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JF - Organic Letters

SN - 1523-7060

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