Organocatalytic Enantioselective (4+2) Annulation of Cyclopropane Carbaldehydes with 2‐Mercapto‐1‐Arylethanones

• Published in: Advanced synthesis & catalysis Vol. 366; no. 5; pp. 1113 - 1119
• Main Authors: Yadav, Neeraj, Hazra, Arijit, Singh, Priyanka, Banerjee, Prabal
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 08.03.2024; Wiley Subscription Services, Inc
• Subjects: (4+2) annulation; Aldehydes; Asymmmetric organocatalysis; Chemical reactions; Chemistry; Chemistry, Applied; Chemistry, Organic; Cycloaddition; Cyclopropane; Enantiomers; kinetic resolution; Organic chemistry; Physical Sciences; Science & Technology; thia-Michael aldol condensation; thia-Michael aldol condensation; DONOR-ACCEPTOR CYCLOPROPANES; TETRAHYDROTHIOPHENES; SULFA-MICHAEL/MICHAEL ADDITION; ASYMMETRIC-SYNTHESIS; STRATEGY; GOLDEN-AGE; CASCADE; (4+2) annulation; DOUBLE-MICHAEL-ADDITION; Asymmmetric organocatalysis; kinetic resolution; CYCLOADDITION REACTION; DERIVATIVES

Here, we report the organocatalytic enantioselective synthesis of dihydrothiopyran derivatives from trans racemic donor–acceptor cyclopropane carbaldehydes (DACCs) and 2‐mercapto‐1‐arylethanone via formal thio (4+2) cycloaddition involving thia‐Michael aldol condensation and annulation. Mechanistic...