Catalytic asymmetric interrupted Attanasi reaction: access to fused 2,3-dihydropyrroles with vicinal quaternary carbons

• Published in: Chemical communications (Cambridge, England) Vol. 59; no. 52; pp. 813 - 816
• Main Authors: Chen, Yun-Xuan, Han, Tian-Jiao, Xiao, Xiao, Wang, Min-Can, Mei, Guang-Jian
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 27.06.2023; Royal Society of Chemistry
• Subjects: Asymmetry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Esters; Physical Sciences; Science & Technology; ORGANIC-SYNTHESIS; DESIGN; (ARYLAZO)ALKENES; AZOALKENES; PYRROLES; METAL-IONS; 1-(ARYLAMINO)PYRROLE DERIVATIVES; 3+2 CYCLOADDITION
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/d3cc02172f

The first catalytic asymmetric interrupted Attanasi reaction has been established. Under the catalysis of a bifunctional organocatalyst, the condensation of cyclic -keto esters with azoalkenes readily occurred, delivering a variety of bicyclic fused 2,3-dihydropyrroles with vicinal quaternary stereogenic centers in good yields and with good to excellent enantioselectivities (27 examples, up to 96% yield and 95% ee). The first catalytic asymmetric interrupted Attanasi reaction has been established, delivering a variety of bicyclic fused 2,3-dihydropyrroles with vicinal quaternary stereogenic centers in good yields and with good to excellent enantioselectivities.