Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of Axially Chiral Compounds†. Issue 7 (24th May 2021)

• Record Type: Journal Article
• Authors: Da, Bing‐Chao; Xiang, Shao‐Hua; Li, Shaoyu; Tan, Bin
• Is Part Of: Chinese journal of chemistry. Volume 39:Issue 7(2021)
• Page Start: 1787
• Page End: 1796
• Publication Date: 2021-05-24
• Subjects: Axial chirality -- Organocatalysis -- Chiral phosphoric acid -- Biaryls -- Asymmetric synthesis; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202000751
• Languages: English
• ISSNs: 1001-604X

Abstract

Abstract: The well‐defined conformational properties of axially chiral compounds bring extraordinary values to an assortment of bioactive molecules, advanced materials, organocatalysts as well as chiral ligands in asymmetric transformations. The demonstrated usefulness and untapped potential of axially chiral structural motifs stimulate increasing efforts to develop novel and efficient approaches for their preparation. In this regard, the chiral phosphoric acids broadly used in asymmetric Brønsted acid catalysis have shown high relevance for atroposelective synthesis as well. Our strong interest in reaction chemistry of atropisomers has established a rewarding research programme in our group. The course of studies will be recounted in this Account, with discussion focused on the use of chiral phosphoric acids to catalyze construction of several key axially chiral structures such as BINAM, BINOL, NOBIN, arylquinones, SPINOL, arylpyrrole analogues and axially chiral alkenes. What is the most favorite and original chemistry developed in your research group? Organocatalytic asymmetric arene C—H functionalization. What is the most important personality for scientific research? Persistence, smart thinking. What are your hobbies? Playing basketball, playing card. What's your favorite book(s)? The Ordinary World by the famous Chinese writer Yao Lu. Who influences you mostly in your life? My parents and my supervisors Prof. Guofu Zhong and Carlos F. Barbas III. How do you supervise your students? I advise my students to work smartly and work hard. Abstract : The well‐defined conformational properties of axially chiral compounds bring extraordinary values to an assortment of bioactive molecules, advanced materials, organocatalysts as well as chiral ligands in asymmetric transformations. The demonstrated usefulness and untapped potential of axially chiral structural motifs stimulate increasing efforts to develop novel and efficient approaches for their preparation. In this regard, the chiral phosphoric acids broadly used in asymmetric Brønsted acid catalysis have shown high relevance for atroposelective synthesis as well. Our strong interest in reaction chemistry of atropisomers has established a rewarding research programme in our group. The course of studies will be recounted in this account, with discussion focused on the use of chiral phosphoric acids to catalyze construction of several key axially chiral structures such as BINAM, BINOL, NOBIN, arylquinones, SPINOL, arylpyrrole analogues and axially chiral alkenes.