Catalytic Asymmetric Mannich/Cyclization of 2‑Isothiocyanato-1-indanones: An Approach to the Synthesis of Bispirocyclic Indanone–Thioimidazolidine–Oxindoles

• Published in: Organic letters Vol. 20; no. 13; pp. 3797 - 3800
• Main Authors: Zhao, Bo-Liang, Du, Da-Ming
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.07.2018; Amer Chemical Soc
• Subjects: chemical structure; Chemistry; Chemistry, Organic; cyclization reactions; enantioselectivity; isothiocyanates; Physical Sciences; Science & Technology; ISOTHIOCYANATO OXINDOLES; DOMINO REACTIONS; ENANTIOSELECTIVE SYNTHESIS; 3-ISOTHIOCYANATO OXINDOLES; CONSTRUCTION; BETA-KETO-ESTERS; MICHAEL ADDITION/CYCLIZATION; POLYCYCLIC SPIROOXINDOLES; HIGHLY EFFICIENT; CASCADE REACTION

This study demonstrates that novel isothiocyanates derived from 1-indanones are useful building blocks in heteroannulation reactions with isatinimines. This convenient Mannich/cyclization cascade reaction serves as a powerful tool for the enantioselective construction of bispirocyclic indanone–thioi...