Design of Efficient Chiral Bifunctional Phase-Transfer Catalysts Possessing an Amino Functionality for Asymmetric Aminations

Suva Paria; Qi Kai Kang; Miho Hatanaka; Keiji Maruoka

doi:10.1021/acscatal.8b03292

Design of Efficient Chiral Bifunctional Phase-Transfer Catalysts Possessing an Amino Functionality for Asymmetric Aminations

Suva Paria, Qi Kai Kang, Miho Hatanaka, Keiji Maruoka

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

24 Citations (Scopus)

Abstract

An efficient, chiral bifunctional phase-transfer catalyst with an intramolecular amino functionality has been designed and successfully applied to highly enantioselective amination of 3-aryloxindoles and 3-arylbenzofuran-2(3H)-ones with bis(adamantyl) azodicarboxylate. Optically active amination products were generally obtained in high yield with high enantioselectivity. The origin of stereoselectivity was explained by means of the DFT calculations. ©

Original language	English
Pages (from-to)	78-82
Number of pages	5
Journal	ACS Catalysis
Volume	9
Issue number	1
DOIs	https://doi.org/10.1021/acscatal.8b03292
Publication status	Published - 2019 Jan 4
Externally published	Yes

Keywords

asymmetric amination
benzofuran-2(3 H)-one
bifunctional catalyst
oxindole
phase-transfer catalyst

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1021/acscatal.8b03292

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title = "Design of Efficient Chiral Bifunctional Phase-Transfer Catalysts Possessing an Amino Functionality for Asymmetric Aminations",

abstract = "An efficient, chiral bifunctional phase-transfer catalyst with an intramolecular amino functionality has been designed and successfully applied to highly enantioselective amination of 3-aryloxindoles and 3-arylbenzofuran-2(3H)-ones with bis(adamantyl) azodicarboxylate. Optically active amination products were generally obtained in high yield with high enantioselectivity. The origin of stereoselectivity was explained by means of the DFT calculations. {\textcopyright}",

keywords = "asymmetric amination, benzofuran-2(3 H)-one, bifunctional catalyst, oxindole, phase-transfer catalyst",

author = "Suva Paria and Kang, {Qi Kai} and Miho Hatanaka and Keiji Maruoka",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP26220803 and JP17H06450 (Hybrid Catalysis). Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2019",

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doi = "10.1021/acscatal.8b03292",

language = "English",

volume = "9",

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T1 - Design of Efficient Chiral Bifunctional Phase-Transfer Catalysts Possessing an Amino Functionality for Asymmetric Aminations

AU - Paria, Suva

AU - Kang, Qi Kai

AU - Hatanaka, Miho

AU - Maruoka, Keiji

PY - 2019/1/4

Y1 - 2019/1/4

N2 - An efficient, chiral bifunctional phase-transfer catalyst with an intramolecular amino functionality has been designed and successfully applied to highly enantioselective amination of 3-aryloxindoles and 3-arylbenzofuran-2(3H)-ones with bis(adamantyl) azodicarboxylate. Optically active amination products were generally obtained in high yield with high enantioselectivity. The origin of stereoselectivity was explained by means of the DFT calculations. ©

AB - An efficient, chiral bifunctional phase-transfer catalyst with an intramolecular amino functionality has been designed and successfully applied to highly enantioselective amination of 3-aryloxindoles and 3-arylbenzofuran-2(3H)-ones with bis(adamantyl) azodicarboxylate. Optically active amination products were generally obtained in high yield with high enantioselectivity. The origin of stereoselectivity was explained by means of the DFT calculations. ©

KW - asymmetric amination

KW - benzofuran-2(3 H)-one

KW - bifunctional catalyst

KW - oxindole

KW - phase-transfer catalyst

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JF - ACS Catalysis

IS - 1

ER -

Design of Efficient Chiral Bifunctional Phase-Transfer Catalysts Possessing an Amino Functionality for Asymmetric Aminations

Abstract

Keywords

ASJC Scopus subject areas

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