Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

Zhenkun Yang; Yu Bao; Jiaxin Huang; Zhengyu Han; Jianwei Sun; Hai Huang

doi:10.1021/acs.orglett.3c02014

Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

Zhenkun Yang, Yu Bao, Jiaxin Huang, Zhengyu Han, Jianwei Sun, Hai Huang^*

^*Corresponding author for this work

Department of Chemistry

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

13 Citations (Scopus)

Abstract

A tandem allylic amination/oxa-Michael addition of vinyl methylene cyclic carbonates (VMCCs) has been developed to construct heterocycles by single palladium catalysis or palladium-organo relay catalysis. In this process, the bisnucleophiles first underwent regioselective allylic amination, and then the second nucleophilic group further completed the hetero-Michael addition reaction to form a series of heterocycles. Among them, the chiral 3,4-dihydro-2H-benzo[b][1,4]oxazines could be produced in medium to high yield with good enantioselectivity under a palladium-organo relay catalysis.

Original language	English
Pages (from-to)	5624-5629
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	30
DOIs	https://doi.org/10.1021/acs.orglett.3c02014
Publication status	Published - 4 Aug 2023

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© 2023 American Chemical Society.

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title = "Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis",

abstract = "A tandem allylic amination/oxa-Michael addition of vinyl methylene cyclic carbonates (VMCCs) has been developed to construct heterocycles by single palladium catalysis or palladium-organo relay catalysis. In this process, the bisnucleophiles first underwent regioselective allylic amination, and then the second nucleophilic group further completed the hetero-Michael addition reaction to form a series of heterocycles. Among them, the chiral 3,4-dihydro-2H-benzo[b][1,4]oxazines could be produced in medium to high yield with good enantioselectivity under a palladium-organo relay catalysis.",

author = "Zhenkun Yang and Yu Bao and Jiaxin Huang and Zhengyu Han and Jianwei Sun and Hai Huang",

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T1 - Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

AU - Yang, Zhenkun

AU - Bao, Yu

AU - Huang, Jiaxin

AU - Han, Zhengyu

AU - Sun, Jianwei

AU - Huang, Hai

PY - 2023/8/4

Y1 - 2023/8/4

N2 - A tandem allylic amination/oxa-Michael addition of vinyl methylene cyclic carbonates (VMCCs) has been developed to construct heterocycles by single palladium catalysis or palladium-organo relay catalysis. In this process, the bisnucleophiles first underwent regioselective allylic amination, and then the second nucleophilic group further completed the hetero-Michael addition reaction to form a series of heterocycles. Among them, the chiral 3,4-dihydro-2H-benzo[b][1,4]oxazines could be produced in medium to high yield with good enantioselectivity under a palladium-organo relay catalysis.

AB - A tandem allylic amination/oxa-Michael addition of vinyl methylene cyclic carbonates (VMCCs) has been developed to construct heterocycles by single palladium catalysis or palladium-organo relay catalysis. In this process, the bisnucleophiles first underwent regioselective allylic amination, and then the second nucleophilic group further completed the hetero-Michael addition reaction to form a series of heterocycles. Among them, the chiral 3,4-dihydro-2H-benzo[b][1,4]oxazines could be produced in medium to high yield with good enantioselectivity under a palladium-organo relay catalysis.

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UR - https://www.scopus.com/pages/publications/85166488260

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DO - 10.1021/acs.orglett.3c02014

M3 - Journal Article

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 30

ER -

Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

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