期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 15, 期 15, 页码 3105-3129出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob02761j
关键词
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资金
- Natural Science Foundation of China [31500562]
- Fundamental Research Funds for the Central Universities [2662016PY122]
- Hubei Cooperative Innovation Center Foundation [2011JH-2014CXTT02]
The Diels-Alder reaction that involves a nitrogen atom in the diene or dienophile is termed the aza-Diels-Alder reaction. As well as the powerful all-carbon Diels-Alder reaction, the aza-Diels-Alder reaction has also played an important role in the total synthesis of natural products. Herein, we review various natural products using an aza-Diels-Alder reaction as a key step to their total synthesis, and divide the syntheses into inter-and intra-molecular aza-Diels-Alder reactions and a retro-aza-Diels-Alder reaction. Inter-and intra-molecular aza-Diels-Alder reactions involve an imine as an electron deficient dienophile and an imine as an electron deficient azadiene. The significance of the aza-Diels-Alder reaction for the construction of a six-membered ring containing nitrogen is tremendous, but the development of asymmetric, in particular catalytic enantioselective intramolecular aza-Diels-Alder reaction in the total synthesis of natural products remains highly challenging, and will no doubt see enormous advances in the future.
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