Organocatalytic asymmetric N-sulfonyl amide C-N bond activation to access axially chiral biaryl amino acids

Guanjie Wang, Qianqian Shi, Wanyao Hu, Tao Chen, Yingying Guo, Zhouli Hu, Minghua Gong, Jingcheng Guo, Donghui Wei (), Zhenqian Fu () and Wei Huang ()
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Guanjie Wang: Nanjing Tech University
Qianqian Shi: Zhengzhou University
Wanyao Hu: Nanjing Tech University
Tao Chen: Nanjing Tech University
Yingying Guo: Nanjing Tech University
Zhouli Hu: Nanjing Tech University
Minghua Gong: Nanjing Tech University
Jingcheng Guo: Nanjing Tech University
Donghui Wei: Zhengzhou University
Zhenqian Fu: Nanjing Tech University
Wei Huang: Nanjing Tech University

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract Amides are among the most fundamental functional groups and essential structural units, widely used in chemistry, biochemistry and material science. Amide synthesis and transformations is a topic of continuous interest in organic chemistry. However, direct catalytic asymmetric activation of amide C-N bonds still remains a long-standing challenge due to high stability of amide linkages. Herein, we describe an organocatalytic asymmetric amide C-N bonds cleavage of N-sulfonyl biaryl lactams under mild conditions, developing a general and practical method for atroposelective construction of axially chiral biaryl amino acids. A structurally diverse set of axially chiral biaryl amino acids are obtained in high yields with excellent enantioselectivities. Moreover, a variety of axially chiral unsymmetrical biaryl organocatalysts are efficiently constructed from the resulting axially chiral biaryl amino acids by our present strategy, and show competitive outcomes in asymmetric reactions.

Date: 2020
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DOI: 10.1038/s41467-020-14799-8

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