Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

Yoshito Takahashi, Risa Yoshii, Takaaki Satou, Noritaka Chida

Research output: Contribution to journal › Article

11 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 languageEnglish
Pages (from-to)5705-5708
Number of pages4
JournalOrganic Letters
Volume20
Issue number18
DOIs
Publication statusPublished - 2018 Sep 21

Fingerprint

Iridium
iridium
Amides
amides
Allylation
Imines
Cycloaddition
Cycloaddition Reaction
cycloaddition
Functional groups
imines
esters
Esters

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides. / Takahashi, Yoshito; Yoshii, Risa; Satou, Takaaki; Chida, Noritaka.

In: Organic Letters, Vol. 20, No. 18, 21.09.2018, p. 5705-5708.

Research output: Contribution to journal › Article

Takahashi, Y, Yoshii, R, Satou, T & Chida, N 2018, 'Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides', Organic Letters, vol. 20, no. 18, pp. 5705-5708. https://doi.org/10.1021/acs.orglett.8b02421
Takahashi Y, Yoshii R, Satou T, Chida N. Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides. Organic Letters. 2018 Sep 21;20(18):5705-5708. https://doi.org/10.1021/acs.orglett.8b02421
Takahashi, Yoshito ; Yoshii, Risa ; Satou, Takaaki ; Chida, Noritaka. / Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides. In: Organic Letters. 2018 ; Vol. 20, No. 18. pp. 5705-5708.
@article{454cedfa130a42d38b7fc1d31ac0f90b,
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 Satou and Noritaka Chida",
year = "2018",
month = "9",
day = "21",
doi = "10.1021/acs.orglett.8b02421",
language = "English",
volume = "20",
pages = "5705--5708",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "18",

}

TY - JOUR

T1 - Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

AU - Takahashi, Yoshito

AU - Yoshii, Risa

AU - Satou, Takaaki

AU - Chida, Noritaka

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.

UR - http://www.scopus.com/inward/record.url?scp=85053499386&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85053499386&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b02421

DO - 10.1021/acs.orglett.8b02421

M3 - Article

C2 - 30192556

AN - SCOPUS:85053499386

VL - 20

SP - 5705

EP - 5708

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 18

ER -

Access to Document