From Peripheral Stereogenic Center to Axial Chirality: Synthesis of 3‐Arylthiophene Atropisomers. Issue 4 (16th November 2022)

• Record Type: Journal Article
• Authors: Li, Lin; Xi, Junwei; Hong, Biqiong; Gu, Zhenhua
• Is Part Of: Advanced synthesis & catalysis. Volume 365:Issue 4(2023)
• Page Start: 594
• Page End: 599
• Publication Date: 2022-11-16
• Subjects: Axial Chirality -- Palladium -- Chirality Transfer -- Ring-Opening -- Atropisomer; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200957
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A practical synthesis of axially chiral biaryls via chirality transfer from peripheral stereogenic carbon centers is reported. In contrast to the traditional aromatization process of a non‐aromatic structure with ipso stereogenic centers, this method is based on a Pd‐catalyzed carbon‐carbon bond cleavage/ring‐opening reaction of optically active 8 H ‐indenothiophen‐8‐ols with an achiral ligand, enabling synthesis of highly functionalized 3‐arylthiophene atropisomers in high enantioselectivity. Abstract :