Asymmetric organocatalytic synthesis of chiral 3, 3-disubstituted oxindoles via a 1, 6-conjugate addition reaction. Issue 29 (11th July 2018)

• Record Type: Journal Article
• Authors: Rahman, Abdul; Zhou, Qiaoxia; Lin, Xufeng
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 29(2018)
• Page Start: 5301
• Page End: 5309
• Publication Date: 2018-07-11
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01169a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The chiral spirocyclic phosphoric acid-catalyzed enantioselective 1, 6-conjugate addition reaction of para -quinone methides derived from N -unprotected isatins with indoles was developed. Abstract : A highly efficient synthesis of chiral 3, 3-disubstituted oxindoles was developed using a chiral spirocyclic phosphoric acid catalyzed 1, 6-conjugate addition reaction of para -quinone methides derived from N -unprotected isatins with indoles. The reaction proceeds under mild reaction conditions to provide indole-containing N -unprotected oxindoles bearing quaternary stereocenters in good yields and with moderate to excellent enantioselectivities (up to 97% ee).