6533b830fe1ef96bd1297461

RESEARCH PRODUCT

Organocatalytic enantioselective 1,6-aza-Michael addition of isoxazolin-5-ones to p-quinone methides

Ricardo ToránCarlos Vila DescalsAmparo Sanz MarcoM. Carmen MuñozJosé Ramón PedroGonzalo Blay Llinares

subject

Compostos heterocíclicsCatàlisiQuímica orgànica

description

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.

yearjournalcountryeditionlanguage
2020-01-01
10.1002/ejoc.201901907https://hdl.handle.net/10550/84746