Abstract
The hetero-Diels–Alder reactions of 1-alkyl-3-( tert-butyldimethylsilyl)oxy-1,3-butadienes with ethyl glyoxylate catalyzed by chiral salen–metal complexes have been studied. With a cobalt(II) complex as the catalyst, the reaction of 1-(2-benzyloxyethyl)-3-( tert-butyldimethylsilyl)oxy-1,3-butadiene with ethyl glyoxylate gave the Diels–Alder product in 75% isolated yield with the endo: exo ratio >99:1 and the enantiomeric excess ≥52%. The effects of temperature, catalyst and solvent are also discussed.
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