Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy

Yu Han Nie; Masaaki Komatsuda; Ping Yang; Chao Zheng; Junichiro Yamaguchi; Shu Li You

doi:10.1021/acs.orglett.2c00129

Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy

Yu Han Nie, Masaaki Komatsuda, Ping Yang, Chao Zheng, Junichiro Yamaguchi, Shu Li You^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

3 Citations (Scopus)

Abstract

Pd-catalyzed asymmetric dearomative arylation of C3-substituted indoles is realized via a desymmetrization strategy. A BINOL-derived chiral phosphoramidite ligand is found to be highly efficient for the stereoselective control in this reaction. This method provides a convenient synthesis of spiroindolenines bearing two stereogenic centers in good yields (up to 98%) with excellent diastereo- and enantioselectivities (up to >20:1 dr and 97% ee), which could also be applied in asymmetric dearomative arylation of the simple C3-tethered indoles.

Original language	English
Pages (from-to)	1481-1485
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.2c00129
Publication status	Published - 2022 Feb 25

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy",

abstract = "Pd-catalyzed asymmetric dearomative arylation of C3-substituted indoles is realized via a desymmetrization strategy. A BINOL-derived chiral phosphoramidite ligand is found to be highly efficient for the stereoselective control in this reaction. This method provides a convenient synthesis of spiroindolenines bearing two stereogenic centers in good yields (up to 98%) with excellent diastereo- and enantioselectivities (up to >20:1 dr and 97% ee), which could also be applied in asymmetric dearomative arylation of the simple C3-tethered indoles.",

author = "Nie, {Yu Han} and Masaaki Komatsuda and Ping Yang and Chao Zheng and Junichiro Yamaguchi and You, {Shu Li}",

note = "Funding Information: We thank the National Key R&D Program of China (2021YFA1500100), NSFC (21821002, 22031012, 91856201), Science and Technology Commission of Shanghai Municipality (19590750400, 21520780100), JSPS KAKENHI Grant Number JP21H05213, JP21K18966, and a Waseda Research Institute for Science and Engineering Grant in Aid for Young Scientists (Early Bird) for generous financial support. Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

year = "2022",

month = feb,

day = "25",

doi = "10.1021/acs.orglett.2c00129",

language = "English",

volume = "24",

pages = "1481--1485",

journal = "Organic Letters",

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T1 - Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy

AU - Nie, Yu Han

AU - Komatsuda, Masaaki

AU - Yang, Ping

AU - Zheng, Chao

AU - Yamaguchi, Junichiro

AU - You, Shu Li

N1 - Funding Information: We thank the National Key R&D Program of China (2021YFA1500100), NSFC (21821002, 22031012, 91856201), Science and Technology Commission of Shanghai Municipality (19590750400, 21520780100), JSPS KAKENHI Grant Number JP21H05213, JP21K18966, and a Waseda Research Institute for Science and Engineering Grant in Aid for Young Scientists (Early Bird) for generous financial support. Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/2/25

Y1 - 2022/2/25

N2 - Pd-catalyzed asymmetric dearomative arylation of C3-substituted indoles is realized via a desymmetrization strategy. A BINOL-derived chiral phosphoramidite ligand is found to be highly efficient for the stereoselective control in this reaction. This method provides a convenient synthesis of spiroindolenines bearing two stereogenic centers in good yields (up to 98%) with excellent diastereo- and enantioselectivities (up to >20:1 dr and 97% ee), which could also be applied in asymmetric dearomative arylation of the simple C3-tethered indoles.

AB - Pd-catalyzed asymmetric dearomative arylation of C3-substituted indoles is realized via a desymmetrization strategy. A BINOL-derived chiral phosphoramidite ligand is found to be highly efficient for the stereoselective control in this reaction. This method provides a convenient synthesis of spiroindolenines bearing two stereogenic centers in good yields (up to 98%) with excellent diastereo- and enantioselectivities (up to >20:1 dr and 97% ee), which could also be applied in asymmetric dearomative arylation of the simple C3-tethered indoles.

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JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy

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