Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters

Minhan Lee; Hoimin Jung; Dongwook Kim; Jung Woo Park; Sukbok Chang

doi:10.1021/jacs.0c04344

Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters

Minhan Lee
, Hoimin Jung
, Dongwook Kim
, Jung Woo Park
, Sukbok Chang

Dept. of Fine Chemistry

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

37 Scopus citations

Abstract

We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.

Original language	English
Pages (from-to)	11999-12004
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	142
Issue number	28
DOIs	https://doi.org/10.1021/jacs.0c04344
State	Published - 15 Jul 2020

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title = "Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters",

abstract = "We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.",

author = "Minhan Lee and Hoimin Jung and Dongwook Kim and Park, \{Jung Woo\} and Sukbok Chang",

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T1 - Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters

AU - Lee, Minhan

AU - Jung, Hoimin

AU - Kim, Dongwook

AU - Park, Jung Woo

AU - Chang, Sukbok

PY - 2020/7/15

Y1 - 2020/7/15

N2 - We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.

AB - We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.

UR - https://www.scopus.com/pages/publications/85088177297

U2 - 10.1021/jacs.0c04344

DO - 10.1021/jacs.0c04344

M3 - Article

C2 - 32605371

AN - SCOPUS:85088177297

SN - 0002-7863

VL - 142

SP - 11999

EP - 12004

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 28

ER -

Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters

Abstract

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