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  • Title: N-heterocyclic carbene catalyzed cyclocondensation of α,β-unsaturated carboxylic acids: enantioselective synthesis of pyrrolidinone and dihydropyridinone derivatives.
    Author: Chen XY, Gao ZH, Song CY, Zhang CL, Wang ZX, Ye S.
    Journal: Angew Chem Int Ed Engl; 2014 Oct 20; 53(43):11611-5. PubMed ID: 25204307.
    Abstract:
    The catalytic cyclocondensation of in situ activated α,β-unsaturated carboxylic acids was developed. N-heterocyclic carbenes efficiently catalyzed the generation of α,β-unsaturated acyl azolium intermediates from α,β-unsaturated carboxylic acids via in situ generated mixed anhydrides for the enantioselective [3+2] and [3+3] cyclocondensation with α-amino ketones and alkyl(aryl)imines, respectively. The corresponding pyrrolidinones and dihydropyridinones were isolated in good yields with high to excellent enantioselectivities.
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