6533b7d4fe1ef96bd1261fe7

RESEARCH PRODUCT

Organocatalytic enantioselective Mannich reaction of isoxazol-5(4H)-ones to isatin-derived ketimines

Ricardo ToránDario PuchánAmparo Sanz-marcoCarlos VilaJosé R. PedroGonzalo Blay

subject

Compostos heterocíclicsCatàlisiOrganic ChemistryPhysical and Theoretical ChemistryBiochemistryQuímica orgànica

description

An efficient organocatalytic asymmetric Mannich reaction between isoxazol-5(4H)-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.

10.1039/d2ob01692chttps://hdl.handle.net/10550/84743