A New Palladium-Catalyzed Intramolecular Allylation to Pyrrolidin-2-ones1
- 22 January 1998
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 63 (3) , 804-807
- https://doi.org/10.1021/jo971849+
Abstract
A novel palladium(0)-catalyzed cyclization to 3,4-disubstituted pyrrolidin-2-ones has been developed. The new approach relies upon the concomitant generation of stabilized acetamide enolate anions and of a π-allyl−palladium appendage, properly tethered by a nitrogen atom. Reaction conditions have been optimized for the methoxycarbonyl-stabilized model reaction [( Z )-2 → 3] and then applied to other substrates. A broad range of acetamide anion stabilizers was shown to allow the desired intramolecular C−C bond formation (MeO2C, MeCO, NC, (EtO)2PO, PhSO2). The cyclizations gave exclusively 5-exo-trig ring closure, thereby affording γ-lactams. All the cyclizations gave the corresponding 3,4-disubstituted pyrrolidin-2-ones with total diastereoselection. Complete trans preference was unequivocally demonstrated for the model reaction via a NOESY experiment.Keywords
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