The gold-catalyzed cyclization of various alpha-amino-ynone derivatives gave the corresponding pyrrolin-4-ones in high yields. Moreover, the use of gold(III) oxide as catalyst allows a moderate to total stereocontrol during the cyclization. These pyrrolin-4-ones are highly useful intermediates for the synthesis of functionalized pyrrolidines and other natural products.
Pyrrole derivatives R 0120Synthesis of Substituted Pyrrolin-4-ones from Amino Acids in Mild Conditions via a Gold-Catalyzed Approach.-The method provides an efficient approach to chiral pyrrolinones such as (IV) and (VII). Subsequent reduction allows stereoselective access to highly substituted pyrrolidines like (IX). -(GOUAULT*, N.; LE ROCH, M.; CORNEE, C.; DAVID, M.; URIAC, P.; J. Org. Chem. 74 (2009) 15, 5614-5617; EA Subst. Lichenique Photoprotect., Fac. Pharm., Univ. Rennes, F-35043 Rennes, Fr.; Eng.) -Jannicke 52-129
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