Asymmetric Organocatalytic Conjugate Addition of Electron‐Rich Phenols and 1,3‐Dicarbonyls to Arylsulfonyl Indoles in an Oil‐Water Biphasic System

• Published in: European journal of organic chemistry Vol. 2019; no. 33; pp. 5815 - 5823
• Main Authors: Han, Jeng‐Liang, Liao, Yu‐Ting, Chang, Chia‐Hao
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 08.09.2019; Wiley Subscription Services, Inc
• Subjects: Asymmetry; Biphasic catalysis; Chemistry; Chemistry, Organic; Conjugates; Indoles; Organocatalysis; Phenols; Physical Sciences; Science & Technology; Stereoselectivity; Synthetic methods; 3,3-DISUBSTITUTED OXINDOLES; 1,6-CONJUGATE ADDITION; GENERATED IN-SITU; ORTHO-QUINONE METHIDES; BETA-SUBSTITUTED TRYPTOPHANS; ENANTIOSELECTIVE MICHAEL ADDITION; Organocatalysis; NONCOVALENT ORGANOCATALYSIS; FLEXIBLE GATEWAY; ALPHA-AMIDO SULFONES; Phenols; Biphasic catalysis; Synthetic methods; Indoles; FRIEDEL-CRAFTS REACTION
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201900962

The asymmetric conjugate addition of electron‐rich phenols and 1,3‐dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts has been established. The chiral 3,3‐disubstituted oxindoles derivatives were obtained in good to high yields (up to 99 % yield) with high enantioselectivies (up to 98 % ee). This study showed that the oil‐water biphasic system contributed to the high efficiency and stereoselectivity. The asymmetric conjugate addition of electron‐rich phenols and 1,3‐dicarbonyls with arylsulfonyl indoles catalyzed by bifunctional organocatalysts have been established. The chiral 3,3‐disubstituted oxindoles derivatives were obtained in good to high yields (up to 99 % yield) with high enantioselectivies (up to 98 % ee). This study showed that oil‐water biphasic system contributed to the high efficiency and stereoselectivity.