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

• Published in: Nature communications Vol. 11; no. 1; p. 946
• Main Authors: Wang, Guanjie, Shi, Qianqian, Hu, Wanyao, Chen, Tao, Guo, Yingying, Hu, Zhouli, Gong, Minghua, Guo, Jingcheng, Wei, Donghui, Fu, Zhenqian, Huang, Wei
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 19.02.2020; Nature Publishing Group; Nature Portfolio
• Subjects: 639/638/403/933; 639/638/77/883; 639/638/77/889; Activation; Amides; Amides - chemistry; Amino acids; Amino Acids - chemical synthesis; Amino Acids - chemistry; Asymmetry; Business competition; Catalysis; Chemical synthesis; Chemistry Techniques, Synthetic - methods; Cleavage; Functional groups; Humanities and Social Sciences; Lactams - chemistry; Linkages; Models, Molecular; Molecular Structure; multidisciplinary; Organic chemistry; Science; Science (multidisciplinary); Stability; Stereoisomerism; Sulfonyl amide
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/s41467-020-14799-8

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. Asymmetric activation of amide bonds remains a challenge due to the high stability of amide linkages. Here, the authors show an organocatalytic asymmetric C-N bond cleavage of N-sulfonyl biaryl lactams under mild conditions, to access axially chiral biaryl amino acids.