期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 358, 期 1, 页码 132-137出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500443
关键词
Bronsted acids; chiral primary amines; iminium catalysis; pyranocoumarins; tandem reactions
资金
- National Natural Science Foundation of China [21372224, 21232008, 21420102003]
- Ministry of Science and Technology of China (973 Program) [2011CB808600]
- Chinese Academy of Sciences
- Shandong independent innovation and achievements transformation major project [2014XGC06001]
A direct enantioselective reaction of cyclopent-2-enone-derived Morita-Baylis-Hillman alcohols with 4-hydroxycoumarins has been developed under the catalysis of a chiral primary amine derived from cinchonine in combination with a Bronsted acid. The reaction provides pyranocoumarin products with three vicinal chiral carbon centers in highly regio-, diastereo- and enantioselectivities through a tandem allylic alkylation/intramolecular oxa-Michael addition.
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