N‐Heterocyclic Carbene Catalyzed Cyclocondensation of α,β‐Unsaturated Carboxylic Acids: Enantioselective Synthesis of Pyrrolidinone and Dihydropyridinone Derivatives |
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| Authors: | Xiang‐Yu Chen Zhong‐Hua Gao Chun‐Yu Song Chun‐Lin Zhang Prof?Dr Zhi‐Xiang Wang Prof?Dr Song Ye |
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| Institution: | 1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China);2. College of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049 (China) |
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| 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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| Keywords: | cyclization heterocycles N‐heterocyclic carbenes organocatalysis synthetic methods |
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