Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.

Guang-Jian Mei; Wenrui Zheng; Theo Goncalves; Xiwen Tang; Kuo-Wei Huang; Yixin Lu

doi:10.1016/j.isci.2020.100873

Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.

Guang-Jian Mei, Wenrui Zheng, Theo Goncalves, Xiwen Tang, Kuo-Wei Huang, Yixin Lu

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

30 Scopus citations

Abstract

Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.

Original language	English (US)
Pages (from-to)	100873
Journal	iScience
Volume	23
Issue number	2
DOIs	https://doi.org/10.1016/j.isci.2020.100873
State	Published - Feb 17 2020

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10.1016/j.isci.2020.100873

https://repository.kaust.edu.sa/bitstream/10754/661577/1/1-s2.0-S2589004220300572-main.pdf

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@article{68c8ef792e4245319ff9442fb1c8680a,

title = "Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.",

abstract = "Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.",

author = "Guang-Jian Mei and Wenrui Zheng and Theo Goncalves and Xiwen Tang and Kuo-Wei Huang and Yixin Lu",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Y.L. thanks the Singapore National Research Foundation, Prime Minister{\textquoteright}s Office for the NRF Investigatorship Award (R-143-000-A15-281). Financial supports from the National University of Singapore (R-143-000-695-114 & C-141-000-092-001) and the National Natural Science Foundation of China (21672158 & 21702077) are also gratefully acknowledged.",

year = "2020",

month = feb,

day = "17",

doi = "10.1016/j.isci.2020.100873",

language = "English (US)",

volume = "23",

pages = "100873",

journal = "iScience",

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publisher = "Elsevier Inc.",

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T1 - Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.

AU - Mei, Guang-Jian

AU - Zheng, Wenrui

AU - Goncalves, Theo

AU - Tang, Xiwen

AU - Huang, Kuo-Wei

AU - Lu, Yixin

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Y.L. thanks the Singapore National Research Foundation, Prime Minister’s Office for the NRF Investigatorship Award (R-143-000-A15-281). Financial supports from the National University of Singapore (R-143-000-695-114 & C-141-000-092-001) and the National Natural Science Foundation of China (21672158 & 21702077) are also gratefully acknowledged.

PY - 2020/2/17

Y1 - 2020/2/17

N2 - Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.

AB - Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.

UR - http://hdl.handle.net/10754/661577

UR - https://linkinghub.elsevier.com/retrieve/pii/S2589004220300572

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DO - 10.1016/j.isci.2020.100873

M3 - Article

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SN - 2589-0042

VL - 23

SP - 100873

JO - iScience

JF - iScience

IS - 2

ER -

Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.

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CCDC 1957145: Experimental Crystal Structure Determination : ethyl 5-(5-cyano-1H-indol-3-yl)-1-[(methoxycarbonyl)amino]-2-methyl-4-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylate

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Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.

Abstract

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CCDC 1957145: Experimental Crystal Structure Determination : ethyl 5-(5-cyano-1H-indol-3-yl)-1-[(methoxycarbonyl)amino]-2-methyl-4-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylate

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