Hydrogen-bond-promoted hetero-Diels-Alder reactions of unactivated ketones.
We report the first examples of hydrogen-bond-promoted acceleration of hetero-Diels-Alder reactions and the use of such catalysis for the hetero-Diels-Alder reactions of simple, unactivated ketones. Several spiro-fused dihydropyans were synthesized in good yields using this procedure. This activation protocol represents an attractive and operationally simple alternative to conventional, Lewis acid catalysis.
Huang
Yong
Y
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Rawal
Viresh H
VH
D000475:Alkenes / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D002725:Chloroform / Q000737:chemistry; D003512:Cyclohexanones / Q000737:chemistry*; D006577:Heterocyclic Oxides / Q000138:chemical synthesis*; D006860:Hydrogen Bonding; D007700:Kinetics; D012997:Solvents / Q000737:chemistry; D013816:Thermodynamics
D000475:Alkenes; D001547:Benzaldehydes; D003512:Cyclohexanones; D006577:Heterocyclic Oxides; D012997:Solvents; C036468:cyclohexanone; D002725:Chloroform; C024896:4-anisaldehyde