Chiral Iodine-Catalyzed Dearomatizative Spirocyclization for the Enantioselective Construction of an All-Carbon Stereogenic Center

• Published in: Chemistry : a European journal Vol. 21; no. 29; pp. 10314 - 10317
• Main Authors: Zhang, Dong-Yang, Xu, Lue, Wu, Hua, Gong, Liu-Zhu
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 13.07.2015; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: asymmetric catalysis; Asymmetry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Construction; dearomatization; Derivatives; hypervalent iodine; Iodine; Level (quantity); organocatalysis; Oxidation; Phenyls; Physical Sciences; Science & Technology; spirooxindoles; hypervalent iodine; ASYMMETRIC DEAROMATIZATION; HYDROXYLATIVE PHENOL DEAROMATIZATION; REAGENTS; IODOARENES; OXIDATIVE DEAROMATIZATION; dearomatization; spirooxindoles; asymmetric catalysis; IN-SITU GENERATION; SPIROLACTONIZATION; organocatalysis; M-CHLOROPERBENZOIC ACID; KETONES; HYPERVALENT
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201501583

The first enantioselective dearomatizative spirocyclization of 1‐hydroxy‐N‐aryl‐2‐naphthamide derivatives has been accomplished by chiral organoiodine catalysis to stereoselectively create an all‐carbon stereogenic center, providing a straightforward approach to access spirooxindole derivatives in good yields and with high to excellent levels of enantioselectivity. Chiral hypervalent phenyl‐λ3‐iodanes generated in situ from the oxidation of the chiral phenyl iodine actually participate in the asymmetric oxidative dearomatizative spirocyclization reaction. The all‐C‐ing I: Enantioselective dearomatizative spirocyclization of 1‐hydroxy‐N‐aryl‐2‐naphthamide derivatives is accomplished by chiral organoiodine catalysis to stereoselectively construct an all‐carbon stereogenic center, providing a straightforward approach to access spirooxindole derivatives in good yields and with high to excellent levels of enantioselectivity.