All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization.

Yanli Yin; Yunqiang Li; Theo Goncalves; Qiangqiang Zhan; Guanghui Wang; Xiaowei Zhao; Baokun Qiao; Kuo-Wei Huang; Zhiyong Jiang

doi:10.1021/jacs.0c08329

All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization.

Yanli Yin, Yunqiang Li, Theo Goncalves, Qiangqiang Zhan, Guanghui Wang, Xiaowei Zhao, Baokun Qiao, Kuo-Wei Huang, Zhiyong Jiang

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

72 Scopus citations

Abstract

A radical-based asymmetric olefin difunctionalization strategy for rapidly forging all-carbon quaternary stereocenters α to diverse azaarenes is reported. Under cooperative photoredox and chiral Brønsted acid catalysis, cyclopropylamines with α-branched 2-vinylazaarenes can undergo a sequential two-step radical process, furnishing various valuable chiral azaarene-substituted cyclopentanes. The use of the rigid and confined C2-symmetric imidodiphosphoric acid catalysts achieves high enantio- and diastereo-selectivities for these asymmetric [3 + 2] cycloadditions.

Original language	English (US)
Journal	Journal of the American Chemical Society
DOIs	https://doi.org/10.1021/jacs.0c08329
State	Published - Nov 5 2020

Bibliographical note

KAUST Repository Item: Exported on 2020-11-09
Acknowledgements: Grants from NSFC (21672052, 21925103) and the PhD Research Foundation of Henan University of Technology (2019BS003) are gratefully acknowledged.

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10.1021/jacs.0c08329

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@article{656a06315826435e9d0ddda920554fb9,

title = "All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization.",

abstract = "A radical-based asymmetric olefin difunctionalization strategy for rapidly forging all-carbon quaternary stereocenters α to diverse azaarenes is reported. Under cooperative photoredox and chiral Br{\o}nsted acid catalysis, cyclopropylamines with α-branched 2-vinylazaarenes can undergo a sequential two-step radical process, furnishing various valuable chiral azaarene-substituted cyclopentanes. The use of the rigid and confined C2-symmetric imidodiphosphoric acid catalysts achieves high enantio- and diastereo-selectivities for these asymmetric [3 + 2] cycloadditions.",

author = "Yanli Yin and Yunqiang Li and Theo Goncalves and Qiangqiang Zhan and Guanghui Wang and Xiaowei Zhao and Baokun Qiao and Kuo-Wei Huang and Zhiyong Jiang",

note = "KAUST Repository Item: Exported on 2020-11-09 Acknowledgements: Grants from NSFC (21672052, 21925103) and the PhD Research Foundation of Henan University of Technology (2019BS003) are gratefully acknowledged.",

year = "2020",

month = nov,

day = "5",

doi = "10.1021/jacs.0c08329",

language = "English (US)",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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T1 - All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization.

AU - Yin, Yanli

AU - Li, Yunqiang

AU - Goncalves, Theo

AU - Zhan, Qiangqiang

AU - Wang, Guanghui

AU - Zhao, Xiaowei

AU - Qiao, Baokun

AU - Huang, Kuo-Wei

AU - Jiang, Zhiyong

N1 - KAUST Repository Item: Exported on 2020-11-09 Acknowledgements: Grants from NSFC (21672052, 21925103) and the PhD Research Foundation of Henan University of Technology (2019BS003) are gratefully acknowledged.

PY - 2020/11/5

Y1 - 2020/11/5

N2 - A radical-based asymmetric olefin difunctionalization strategy for rapidly forging all-carbon quaternary stereocenters α to diverse azaarenes is reported. Under cooperative photoredox and chiral Brønsted acid catalysis, cyclopropylamines with α-branched 2-vinylazaarenes can undergo a sequential two-step radical process, furnishing various valuable chiral azaarene-substituted cyclopentanes. The use of the rigid and confined C2-symmetric imidodiphosphoric acid catalysts achieves high enantio- and diastereo-selectivities for these asymmetric [3 + 2] cycloadditions.

AB - A radical-based asymmetric olefin difunctionalization strategy for rapidly forging all-carbon quaternary stereocenters α to diverse azaarenes is reported. Under cooperative photoredox and chiral Brønsted acid catalysis, cyclopropylamines with α-branched 2-vinylazaarenes can undergo a sequential two-step radical process, furnishing various valuable chiral azaarene-substituted cyclopentanes. The use of the rigid and confined C2-symmetric imidodiphosphoric acid catalysts achieves high enantio- and diastereo-selectivities for these asymmetric [3 + 2] cycloadditions.

UR - http://hdl.handle.net/10754/665859

UR - https://pubs.acs.org/doi/10.1021/jacs.0c08329

U2 - 10.1021/jacs.0c08329

DO - 10.1021/jacs.0c08329

M3 - Article

C2 - 33152237

SN - 0002-7863

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

ER -

All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization.

Abstract

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CCDC 1959654: Experimental Crystal Structure Determination : 2-(2-oxo-1-phenylcyclopentan-1-yl)pyridine N-oxide

CCDC 1959655: Experimental Crystal Structure Determination : N-[2-(4-bromophenyl)-2-(1-methyl-1H-imidazol-2-yl)cyclopentyl]aniline

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All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization.

Abstract

Bibliographical note

Access to Document

Other files and links

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Datasets

CCDC 1959654: Experimental Crystal Structure Determination : 2-(2-oxo-1-phenylcyclopentan-1-yl)pyridine N-oxide

CCDC 1959655: Experimental Crystal Structure Determination : N-[2-(4-bromophenyl)-2-(1-methyl-1H-imidazol-2-yl)cyclopentyl]aniline

Cite this