Rhodium‐Catalyzed Enantioselective Synthesis of β‐Amino Alcohols via Desymmetrization of <i>gem</i>‐Dimethyl Groups

Bingxian Liu, Pengfei Xie, Jie Zhao, Juanjuan Wang, Manman Wang, Yuqin Jiang, Junbiao Chang, Xingwei Li

doi:10.1002/anie.202014080

Rhodium‐Catalyzed Enantioselective Synthesis of β‐Amino Alcohols via Desymmetrization of <i>gem</i>‐Dimethyl Groups

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Bingxian Liu

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China
Pengfei Xie

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China
Jie Zhao

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China
Juanjuan Wang

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China
Manman Wang

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China
Yuqin Jiang

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China
Junbiao Chang

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China
Xingwei Li

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China

書誌事項

公開日: 2021-03

権利情報

http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/anie.202014080

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Desymmetrization of <jats:italic>gem</jats:italic>‐dimethyl groups en route to the rhodium(III)‐catalyzed enantioselective sp<jats:sup>3</jats:sup> C−H amidation is reported. Synthetically important β‐amino alcohol derivatives were accessed in moderate to good yields and high enantioselectivity. The high enantioselectivity is enabled by an appropriate oxime directing group, sterically biased <jats:italic>gem</jats:italic>‐groups in the C−H substrate, and high reactivity of the amidating reagent.</jats:p>