Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis

Taoda Shi; Shenghan Teng; Alavala Gopi Krishna Reddy; Xin Guo; Yueteng Zhang; Kohlson T. Moore; Thomas Buckley; Damian J. Mason; Wei Wang; Eli Chapman; Wenhao Hu

doi:10.1039/c9ob01903k

Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis

Taoda Shi, Shenghan Teng, Alavala Gopi Krishna Reddy, Xin Guo, Yueteng Zhang, Kohlson T. Moore, Thomas Buckley, Damian J. Mason, Wei Wang, Eli Chapman, Wenhao Hu

Pharmacology and Toxicology

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

4 Scopus citations

Abstract

We report a bifunctional Ag catalyst promoted intramolecular capture of oxonium ylides with alkynes for the enantioselective synthesis of 2,5-dihydrofurans. This represents unprecedented synergistic catalysis of a bifunctional Ag catalyst. Mechanistic studies revealed that [(R)-3,5-DM-BINAP](AgSbF₆)₂ (9) is likely to be the active catalytic species and that the reaction involves second order kinetics with respect to 9, suggesting that two molecules of 9 are involved in the intramolecular trapping of a Ag-associated oxonium ylide with a Ag-activated alkyne. Based on our mechanistic hypothesis, we further optimized the reaction, rendering a facile approach to 2,5-dihydrofurans in good to excellent yields in a highly chemo- and enantioselective fashion.

Original language	English (US)
Pages (from-to)	8737-8744
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	17
Issue number	38
DOIs	https://doi.org/10.1039/c9ob01903k
State	Published - 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis. / Shi, Taoda; Teng, Shenghan; Gopi Krishna Reddy, Alavala; Guo, Xin; Zhang, Yueteng; Moore, Kohlson T.; Buckley, Thomas; Mason, Damian J.; Wang, Wei; Chapman, Eli; Hu, Wenhao.

In: Organic and Biomolecular Chemistry, Vol. 17, No. 38, 2019, p. 8737-8744.

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

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title = "Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis",

abstract = "We report a bifunctional Ag catalyst promoted intramolecular capture of oxonium ylides with alkynes for the enantioselective synthesis of 2,5-dihydrofurans. This represents unprecedented synergistic catalysis of a bifunctional Ag catalyst. Mechanistic studies revealed that [(R)-3,5-DM-BINAP](AgSbF6)2 (9) is likely to be the active catalytic species and that the reaction involves second order kinetics with respect to 9, suggesting that two molecules of 9 are involved in the intramolecular trapping of a Ag-associated oxonium ylide with a Ag-activated alkyne. Based on our mechanistic hypothesis, we further optimized the reaction, rendering a facile approach to 2,5-dihydrofurans in good to excellent yields in a highly chemo- and enantioselective fashion.",

author = "Taoda Shi and Shenghan Teng and {Gopi Krishna Reddy}, Alavala and Xin Guo and Yueteng Zhang and Moore, {Kohlson T.} and Thomas Buckley and Mason, {Damian J.} and Wei Wang and Eli Chapman and Wenhao Hu",

note = "Funding Information: We are grateful for the financial support from NSFC 21332003 (WH), the Program for Guangdong Introducing Innovative and Enterpreneurial Teams 2016ZT06Y337 (WH), the University of Arizona (EC), and the China Scholarship Council (TS). We also thank members of the Chapman and Hu labs for helpful discussions. Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",

year = "2019",

doi = "10.1039/c9ob01903k",

language = "English (US)",

volume = "17",

pages = "8737--8744",

journal = "Organic and Biomolecular Chemistry",

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T1 - Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis

AU - Shi, Taoda

AU - Teng, Shenghan

AU - Gopi Krishna Reddy, Alavala

AU - Guo, Xin

AU - Zhang, Yueteng

AU - Moore, Kohlson T.

AU - Buckley, Thomas

AU - Mason, Damian J.

AU - Wang, Wei

AU - Chapman, Eli

AU - Hu, Wenhao

N1 - Funding Information: We are grateful for the financial support from NSFC 21332003 (WH), the Program for Guangdong Introducing Innovative and Enterpreneurial Teams 2016ZT06Y337 (WH), the University of Arizona (EC), and the China Scholarship Council (TS). We also thank members of the Chapman and Hu labs for helpful discussions. Publisher Copyright: © 2019 The Royal Society of Chemistry. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

PY - 2019

Y1 - 2019

N2 - We report a bifunctional Ag catalyst promoted intramolecular capture of oxonium ylides with alkynes for the enantioselective synthesis of 2,5-dihydrofurans. This represents unprecedented synergistic catalysis of a bifunctional Ag catalyst. Mechanistic studies revealed that [(R)-3,5-DM-BINAP](AgSbF6)2 (9) is likely to be the active catalytic species and that the reaction involves second order kinetics with respect to 9, suggesting that two molecules of 9 are involved in the intramolecular trapping of a Ag-associated oxonium ylide with a Ag-activated alkyne. Based on our mechanistic hypothesis, we further optimized the reaction, rendering a facile approach to 2,5-dihydrofurans in good to excellent yields in a highly chemo- and enantioselective fashion.

AB - We report a bifunctional Ag catalyst promoted intramolecular capture of oxonium ylides with alkynes for the enantioselective synthesis of 2,5-dihydrofurans. This represents unprecedented synergistic catalysis of a bifunctional Ag catalyst. Mechanistic studies revealed that [(R)-3,5-DM-BINAP](AgSbF6)2 (9) is likely to be the active catalytic species and that the reaction involves second order kinetics with respect to 9, suggesting that two molecules of 9 are involved in the intramolecular trapping of a Ag-associated oxonium ylide with a Ag-activated alkyne. Based on our mechanistic hypothesis, we further optimized the reaction, rendering a facile approach to 2,5-dihydrofurans in good to excellent yields in a highly chemo- and enantioselective fashion.

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VL - 17

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 38

ER -

Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis

Abstract

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