期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 11, 页码 5951-5957出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00597
关键词
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资金
- National Natural Science Foundation of China [21372217]
- National Basic Research Program of China (973 Program) [2010CB833300]
- Sichuan Youth Science and Technology Foundation [2013JQ0021, 2015JQ0041]
An efficient and unprecedented organocatalytic asymmetric reaction of 3-pyrrolyl-oxindoles with alpha,beta-unsaturated aldehydes to generate spirocyclic oxindole compounds was developed. The reactions were catalyzed by diphenylprolinol silyl ether and 2-fluorobenzoic acid via an asymmetric Michael/Friedel-Crafts cascade process, followed by dehydration with p-toluenesulfonic acid to afford a wide variety of structurally diverse Spiro [5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindole] derivatives in high yields (up to 93%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 97% ee).
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