Bisoxazoline-Lewis acid-catalyzed direct-electron demand oxo-hetero-Diels-Alder reactions of N-oxy-pyridine aldehyde and ketone derivatives.
A general catalytic oxo-hetero-Diels-Alder reaction for pro-chiral aldehyde and ketone N-oxy-pyridines is presented. The catalytic and asymmetric oxo-hetero-Diels-Alder reaction of electron-rich dienes with N-oxy-pyridine-2-carbaldehyde and ketone derivatives, catalyzed by chiral copper(II)-bisoxazoline complexes, gives optically active six-membered oxygen heterocycles in moderate to good yields and with excellent enantioselectivities.
Landa
Aitor
A
Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.
Richter
Bo
B
Johansen
Rasmus Lyng
RL
Minkkilä
Anna
A
Jørgensen
Karl Anker
KA
D000143:Acids / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D004952:Esters / Q000737:chemistry; D006860:Hydrogen Bonding; D007659:Ketones / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D000143:Acids; D000447:Aldehydes; D004952:Esters; D007659:Ketones; D010080:Oxazoles; D011725:Pyridines; C023666:pyridine; D010100:Oxygen