Organocatalytic Enantioselective 1, 6‐aza‐Michael Addition of Isoxazolin‐5‐ones to p‐Quinone Methides. Issue 5 (27th January 2020)

• Record Type: Journal Article
• Authors: Torán, Ricardo; Vila, Carlos; Sanz‐Marco, Amparo; Muñoz, M. Carmen; Pedro, José R.; Blay, Gonzalo
• Is Part Of: European journal of inorganic chemistry. Issue 5(2020)
• Page Start: 627
• Page End: 630
• Publication Date: 2020-01-27
• Subjects: Asymmetric catalysis -- Enantioselectivity -- Conjugate addition -- Heterocycles -- Alkylation; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejoc.201901907
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract : A thiourea‐Brønsted base bifunctional catalyst allowed the enantioselective 1, 6‐ aza ‐Michael addition of isoxazolin‐5‐ones to p ‐quinone methides to give isoxazolin‐5‐ones having a chiral diarylmethyl moiety attached to the N atom with fair to good yields and enantiomeric excesses. To the best of our knowledge this reaction represents the first example of enantioselective N ‐alkylation of isoxazolin‐5‐ones as well as the first example of enantioselective 1, 6‐ aza ‐Michael reaction involving p ‐quinone methides. Abstract : A bifunctional organocatalyst allowed the enantioselective 1, 6‐ aza ‐Michael addition of isoxazolin‐5‐ones to p ‐quinone methides to give isoxazolin‐5‐ones having a chiral diarylmethyl moiety attached to the N atom with fair to good yields and enantiomeric excesses.