Carbene-Catalyzed Direct O-Functionalization of Ketone: Atroposelective Access to Non-C2-Symmetric Binaphthyls

Bivas Mondal; Hang Chen; Rakesh Maiti; Hongling Wang; Hui Cai; Chengli Mou; Lin Hao; Huifang Chai; Yonggui Robin Chi

doi:10.1021/acs.orglett.3c03141

Carbene-Catalyzed Direct O-Functionalization of Ketone: Atroposelective Access to Non-C₂-Symmetric Binaphthyls

Bivas Mondal, Hang Chen, Rakesh Maiti, Hongling Wang, Hui Cai, Chengli Mou, Lin Hao, Huifang Chai^*, Yonggui Robin Chi^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

Disclosed here is NHC-catalyzed direct intermolecular trapping of the ketone oxygen atom with the acyl azolium intermediate. The overall reaction is a dynamic kinetic resolution process that converts ketone to the corresponding enol ester with well-controlled axial chirality. Our reaction eventually affords non-C₂-symmetric binaphthyl derivatives with important applications, such as in the area of asymmetric catalysis.

Original language	English
Pages (from-to)	8252-8257
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	46
DOIs	https://doi.org/10.1021/acs.orglett.3c03141
Publication status	Published - Nov 24 2023
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.3c03141

Cite this

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title = "Carbene-Catalyzed Direct O-Functionalization of Ketone: Atroposelective Access to Non-C2-Symmetric Binaphthyls",

abstract = "Disclosed here is NHC-catalyzed direct intermolecular trapping of the ketone oxygen atom with the acyl azolium intermediate. The overall reaction is a dynamic kinetic resolution process that converts ketone to the corresponding enol ester with well-controlled axial chirality. Our reaction eventually affords non-C2-symmetric binaphthyl derivatives with important applications, such as in the area of asymmetric catalysis.",

author = "Bivas Mondal and Hang Chen and Rakesh Maiti and Hongling Wang and Hui Cai and Chengli Mou and Lin Hao and Huifang Chai and Chi, {Yonggui Robin}",

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doi = "10.1021/acs.orglett.3c03141",

language = "English",

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TY - JOUR

T1 - Carbene-Catalyzed Direct O-Functionalization of Ketone

T2 - Atroposelective Access to Non-C2-Symmetric Binaphthyls

AU - Mondal, Bivas

AU - Chen, Hang

AU - Maiti, Rakesh

AU - Wang, Hongling

AU - Cai, Hui

AU - Mou, Chengli

AU - Hao, Lin

AU - Chai, Huifang

AU - Chi, Yonggui Robin

PY - 2023/11/24

Y1 - 2023/11/24

N2 - Disclosed here is NHC-catalyzed direct intermolecular trapping of the ketone oxygen atom with the acyl azolium intermediate. The overall reaction is a dynamic kinetic resolution process that converts ketone to the corresponding enol ester with well-controlled axial chirality. Our reaction eventually affords non-C2-symmetric binaphthyl derivatives with important applications, such as in the area of asymmetric catalysis.

AB - Disclosed here is NHC-catalyzed direct intermolecular trapping of the ketone oxygen atom with the acyl azolium intermediate. The overall reaction is a dynamic kinetic resolution process that converts ketone to the corresponding enol ester with well-controlled axial chirality. Our reaction eventually affords non-C2-symmetric binaphthyl derivatives with important applications, such as in the area of asymmetric catalysis.

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U2 - 10.1021/acs.orglett.3c03141

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SP - 8252

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JO - Organic Letters

JF - Organic Letters

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