Abstract
Reported is the gold-catalyzed synthesis of 2,4,5-trisubstituted oxazoles 3 via the formal [3+2] cycloaddition of ynamides 1 with pyridine-N-aminides 2. N-Alkyl, -benzyl, and -aryl groups on the ynamide are all well tolerated. Excellent chemoselectivity in the addition to the ynamide π-system is observed, even in the presence of another alkene or alkyne (R² = CH2C≡CTMS, allyl). With regard to alkyne R³ substitution, both alkyl (including a primary alkyl bromide) and conjugated systems perform equally well. The reaction is not limited to ynamides since the cyclization of an ynol ether was shown to give 4-ethoxyoxazole 4 in moderate yield.
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