1.
J Org Chem
; 86(9): 6826-6839, 2021 May 07.
Artigo
em Inglês
| MEDLINE
| ID: mdl-33904749
RESUMO
Organocatalytic enantioselective intramolecular oxa-Michael reactions of benzyl alcohol bearing α,ß-unsaturated carbonyls as Michael acceptors are presented herein. Using cinchona squaramide-based organocatalyst, enones as well as α,ß-unsaturated esters containing benzyl alcohol provided their corresponding 1,3-dihydroisobenzofuranyl-1-methylene ketones and 1,3-dihydroisobenzofuranyl-1-methylene esters in excellent yields with high enantioselectivities. In addition, enantioenriched 1,3-dihydroisobenzofuranyl-1-methylene ketone could be obtained from the Wittig/oxa-Michael reaction cascade of 1,3-dihydro-2-benzofuran-1-ol.