Catalytic enantioselective domino oxa-michael/aldol condensations: asymmetric synthesis of benzopyran derivatives.
The first direct organocatalytic asymmetric domino oxa-Michael/aldol condensation reaction is presented. The unprecedentedly simple, chiral, pyrrolidine-catalyzed asymmetric domino reactions between salicylic aldehyde derivatives and alpha,beta-unsaturated aldehydes proceed with high chemo- and enantioselectivities to give the corresponding chromene-3-carbaldehyde derivatives in high yields and with ee values of 83-98%.
Sundén
Henrik
H
Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden.
Ibrahem
Ismail
I
Zhao
Gui-Ling
GL
Eriksson
Lars
L
Córdova
Armando
A
D000447:Aldehydes / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D001547:Benzaldehydes; D001578:Benzopyrans; D006571:Heterocyclic Compounds; D012997:Solvents