Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts
摘要：
Helical-chiral double hydrogen bond donor catalysts promote the nitroalkene Diels-Alder reaction in an enantio-and periselective manner. This represents the first asymmetric catalytic nitroalkene Diels-Alder reaction via LUMO-lowering catalysis. To gain an insight into this new process, the substrate scope of our catalyst was investigated by exploiting readily available 5-substituted pentamethylcyclopentadienes. The catalyst was found to tolerate dienes with different steric demands as well as dienes substituted with heteroatoms. The synthetic utility of 5-substituted pentamethylcyclopentadienes is rather limited, and thus we have developed a three-step route to 1,4,5,5-tetrasubstituted cyclopentadienes from commercially available ketones.
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关键词：
HIGHLY FUNCTIONALIZED CYCLOPENTENES ASYMMETRIC CATALYSIS 2-DISUBSTITUTED 1 3-CYCLOPENTANEDIONES 2-AMINOPYRIDINIUM IONS CARBONYL METHYLENATION KETONES ACID NITROETHYLENE
DOI：
10.3390/molecules18089982
被引量：
年份：
2013
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