Catalyst-controlled diastereoselective hetero-Diels-Alder reactions.
[reaction: see text] The diastereoselective hetero-Diels-Alder reaction between Danishefsky's diene and chiral aldehydes is catalyzed by chiral chromium-Schiff base complexes. High levels of catalyst control are obtained in several cases, allowing access to all four stereoisomeric products through appropriate choice of aldehyde and catalyst enantiomers.
Joly
Guy D
GD
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Jacobsen
Eric N
EN
D000447:Aldehydes; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D011714:Pyrans / Q000138:chemical synthesis*; D012545:Schiff Bases; D013237:Stereoisomerism
D000447:Aldehydes; D007202:Indicators and Reagents; D011714:Pyrans; D012545:Schiff Bases; C014634:lactaldehyde