期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 15, 页码 4201-4205出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700045
关键词
heterocycles; lactones; N-heterocyclic carbenes; organocatalysis; reaction mechanisms
资金
- National Natural Science Foundation of China [21132003, 21472028]
- Singapore National Research Foundation [NRF-NRFI2016-06]
- Ministry of Education of Singapore [MOE2013-T2-2-003, MOE2016-T2-1-032]
- Nanyang Technological University (NTU, Singapore)
- China's Ministry of Education
- Thousand Talent Plan
- Guizhou Province Returned Oversea Student Science and Technology Activity Program
- Science and Technology of Guizhou Province
- Guizhou University
A carbene-catalyzed intermolecular C-N bond formation, which initiates a highly selective cascade reaction for the synthesis of pyrrolidine fused beta-lactones, is disclosed. The nitrogen-containing bicyclic beta-lactone products are obtained with good yields and excellent stereoselectivities. Synthetic transformations of the reaction products into useful functional molecules, such as amino catalysts, can be efficiently realized under mild reaction conditions. Mechanistically, this study provides insights into modulating the reactivities of heteroatoms, such as nitrogen atoms, in challenging carbene-catalyzed asymmetric carbon-heteroatom bond-forming reactions.
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