Diastereoselective Synthesis of Densely Functionalized 3a,8a-Dihydro-8 H-furo[3,2- a]pyrrolizines through One-Pot Three-Component Assembly

Sunhee Lee; Sunmi Kim; Seok Hyun Yoon; Anuradha Dagar; Ikyon Kim

doi:10.1021/acs.joc.1c01315

Diastereoselective Synthesis of Densely Functionalized 3a,8a-Dihydro-8 H-furo[3,2- a]pyrrolizines through One-Pot Three-Component Assembly

Sunhee Lee, Sunmi Kim, Seok Hyun Yoon, Anuradha Dagar, Ikyon Kim

Department of Pharmacy

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

2 Citations (Scopus)

Abstract

A new domino mode of assembly was discovered from the one-pot three-component reactions of pyrrole derivatives, active methylene compounds (malononitrile, methyl cyanoacetate, or ethyl cyanoacetate), and sodium cyanide in the presence of piperidinium acetate in EtOH at room temperature, leading to a novel tricyclic skeleton in excellent yield under mild and eco-friendly conditions. This well-choreographed domino process enabled formation of multiple bonds (three C-C and one C-O) for consecutive construction of two rings (pyrrolidine and dihydrofuran) in a diastereoselective manner.

Original language	English
Pages (from-to)	12367-12377
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	86
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.1c01315
Publication status	Published - 2021 Sept 3

Bibliographical note

Funding Information:
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support.

Publisher Copyright:
© 2021 American Chemical Society.

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/acs.joc.1c01315

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title = "Diastereoselective Synthesis of Densely Functionalized 3a,8a-Dihydro-8 H-furo[3,2- a]pyrrolizines through One-Pot Three-Component Assembly",

abstract = "A new domino mode of assembly was discovered from the one-pot three-component reactions of pyrrole derivatives, active methylene compounds (malononitrile, methyl cyanoacetate, or ethyl cyanoacetate), and sodium cyanide in the presence of piperidinium acetate in EtOH at room temperature, leading to a novel tricyclic skeleton in excellent yield under mild and eco-friendly conditions. This well-choreographed domino process enabled formation of multiple bonds (three C-C and one C-O) for consecutive construction of two rings (pyrrolidine and dihydrofuran) in a diastereoselective manner.",

author = "Sunhee Lee and Sunmi Kim and Yoon, {Seok Hyun} and Anuradha Dagar and Ikyon Kim",

note = "Funding Information: We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

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doi = "10.1021/acs.joc.1c01315",

language = "English",

volume = "86",

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journal = "Journal of Organic Chemistry",

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AU - Lee, Sunhee

AU - Kim, Sunmi

AU - Yoon, Seok Hyun

AU - Dagar, Anuradha

AU - Kim, Ikyon

N1 - Funding Information: We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support. Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/9/3

Y1 - 2021/9/3

N2 - A new domino mode of assembly was discovered from the one-pot three-component reactions of pyrrole derivatives, active methylene compounds (malononitrile, methyl cyanoacetate, or ethyl cyanoacetate), and sodium cyanide in the presence of piperidinium acetate in EtOH at room temperature, leading to a novel tricyclic skeleton in excellent yield under mild and eco-friendly conditions. This well-choreographed domino process enabled formation of multiple bonds (three C-C and one C-O) for consecutive construction of two rings (pyrrolidine and dihydrofuran) in a diastereoselective manner.

AB - A new domino mode of assembly was discovered from the one-pot three-component reactions of pyrrole derivatives, active methylene compounds (malononitrile, methyl cyanoacetate, or ethyl cyanoacetate), and sodium cyanide in the presence of piperidinium acetate in EtOH at room temperature, leading to a novel tricyclic skeleton in excellent yield under mild and eco-friendly conditions. This well-choreographed domino process enabled formation of multiple bonds (three C-C and one C-O) for consecutive construction of two rings (pyrrolidine and dihydrofuran) in a diastereoselective manner.

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SN - 0022-3263

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SP - 12367

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ER -

Diastereoselective Synthesis of Densely Functionalized 3a,8a-Dihydro-8 H-furo[3,2- a]pyrrolizines through One-Pot Three-Component Assembly

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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