Highly Diastereo- and Enantioselective Synthesis of Isoxazolone-Spirooxindoles via Squaramide-Catalyzed Cascade Michael/Michael Addition Reactions

• Published in: Journal of organic chemistry Vol. 85; no. 23; pp. 15325 - 15336
• Main Authors: Wang, Yu, Du, Da-Ming
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 04.12.2020; Amer Chemical Soc
• Subjects: acrylates; ammonium chloride; chemical reactions; Chemistry; Chemistry, Organic; enantioselective synthesis; enantioselectivity; organic chemistry; Physical Sciences; Science & Technology; ORGANOCATALYSTS; ACID; CITRINADIN-A; MICHAEL-ADDITION; ONE-POT; 3-HYDROXYOXINDOLES; BISPIROOXINDOLES; 3-AMINO; DERIVATIVES

A highly enantioselective [3+2] annulation of 3-((2-oxoindolin-3-yl)­oxy)­acrylates with isoxazol-5­(4H)-ones has been accomplished by squaramide-catalyzed cascade Michael/Michael addition reactions under mild conditions. The corresponding isoxazolone-spirooxindoles with four continuous stereocenter...