Ternary Aldehyde–Copper–Iridium Catalysis Enables Stereodivergent Allylation via α-C-H Functionalization of Primary Amines
Zijiao Liu
Shanghai University of Medicine & Health Sciences Affiliated Sixth People's Hospital South Campus, Shanghai, 201499 China
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Both authors contributed equally to this work.
Search for more papers by this authorDr. Panpan Li
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Both authors contributed equally to this work.
Search for more papers by this authorHaoyang Wang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorDr. Jiacheng Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Prof. Xiaohong Huo
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
E-mail: [email protected]; [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Prof. Zhen-Liang Sun
Shanghai University of Medicine & Health Sciences Affiliated Sixth People's Hospital South Campus, Shanghai, 201499 China
E-mail: [email protected]; [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Prof. Wanbin Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
E-mail: [email protected]; [email protected]; [email protected]
Search for more papers by this authorZijiao Liu
Shanghai University of Medicine & Health Sciences Affiliated Sixth People's Hospital South Campus, Shanghai, 201499 China
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Both authors contributed equally to this work.
Search for more papers by this authorDr. Panpan Li
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Both authors contributed equally to this work.
Search for more papers by this authorHaoyang Wang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorDr. Jiacheng Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Prof. Xiaohong Huo
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
E-mail: [email protected]; [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Prof. Zhen-Liang Sun
Shanghai University of Medicine & Health Sciences Affiliated Sixth People's Hospital South Campus, Shanghai, 201499 China
E-mail: [email protected]; [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Prof. Wanbin Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
E-mail: [email protected]; [email protected]; [email protected]
Search for more papers by this authorGraphical Abstract
A direct enantio- and diastereodivergent α-allylation of unprotected primary amines has been developed using aldehyde/Cu/Ir ternary catalysis. This catalytic system enables the synthesis of α-tertiary primary amines bearing vicinal stereocenters in high yields with excellent stereoselectivities. Notably, this method establishes a sophisticated asymmetric induction model for asymmetric α-C-H functionalization of unprotected primary amines.
Abstract
α-Chiral primary amines are recognized as one of the most valuable and versatile synthetic intermediates, widely utilized in the construction of diverse amine-containing natural products, pharmaceuticals, and agrochemicals. The direct asymmetric α-C-H functionalization of unprotected primary amines is the most straightforward method for creating these motifs. However, this transformation remains underdeveloped, particularly in stereodivergent synthesis of primary amines with multiple stereocenters. Herein, we report an aldehyde/copper/iridium ternary catalytic system, which was successfully employed for the direct enantio- and diastereodivergent α-allylation of primary α-amino-chromanone without requiring additional protection or activation of the NH2 group. A wide range of α-tertiary primary amines bearing vicinal stereocenters were prepared in high yields with excellent enantio- and diastereoselectivities (generally >20:1 dr and >99% ee). Notably, all four stereoisomers of the α-tertiary amines can be readily prepared by simply switching the configuration combinations of the two chiral metal catalysts. Furthermore, the asymmetric induction model for the α-C-H functionalization of primary amines was meticulously elucidated through comprehensive density functional theory (DFT) calculations.
Conflict of Interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
Supporting Information
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