Organocatalytic enantioselective Mannich reaction of isoxazol-5(4H)-ones to isatin-derived ketimines. Issue 43 (14th October 2022)

• Record Type: Journal Article
• Authors: Torán, Ricardo; Puchán, Dario; Sanz-Marco, Amparo; Vila, Carlos; Pedro, José R.; Blay, Gonzalo
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 43(2022)
• Page Start: 8395
• Page End: 8399
• Publication Date: 2022-10-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01692c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient organocatalytic asymmetric Mannich reaction between isoxazol-5(4 H )-ones and isatin-derived ketimines has been developed. Abstract : An efficient organocatalytic asymmetric Mannich reaction between isoxazol-5(4 H )-ones and isatin-derived ketimines has been developed. A bifunctional squaramide/Brønsted base organocatalyst catalyzed the enantioselective Mannich addition to afford chiral 3-aminooxindoles bearing a tetrasubstituted stereocenter at C3 decorated with an isoxazole moiety in good yields and with excellent enantioselectivities. Additionally, several synthetic transformations were described showing the versatility of the prepared compounds.