Catalytic, Enantioselective Hetero-Diels-Alder Reaction with Novel, Chiral Bis-Titanium(IV) Catalyst

Abstract

Our recently designed chiral bis-titanium(IV) catalyst can be successfully utilized for the catalytic enantioselective hetero-Diels-Alder reaction of aldehyde and Danishefsky’s diene. The high asymmetric induction is achievable in the case of sterically less hindered aldehydes.

Key words

hetero-Diels-Alder - asymmetric synthesis - catalyst - titanium(IV) complex

References

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4

The hetero-Diels-Alder reaction of phenylpropargyl aldehyde 3 (R = C≡ CPh) proceeded smoothly with a chiral mono-Ti(IV) complex 2 (10 mol%) to give adduct 4 (R = C≡ CPh) in 47% yield. In contrast, however, the reactivity of the hetero-Diels-Alder reaction of benzaldehyde 3 (R = Ph) are lowered (e.g., 29% yield) under similar reaction condition with a chiral mono-Ti(IV) 2 (10 mol%).