期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 358, 期 24, 页码 3992-3998出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600782
关键词
asymmetric catalysis; Michael addition; organocatalysis; spirooxindoles; squaramides
资金
- National Natural Science Foundation of China [21272024]
A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of spirotetrahydrofuran bispirooxindoles was developed. The products were obtained in moderate to excellent yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, >99% ee). This straightforward process serves as a powerful method for the enantioselective construction of potentially bioactive bispirooxindoles in which two of the four contiguous chiral centers are spiro all-carbon quaternary centers on a single tetrahydrofuran ring. Meanwhile, the synthetic practicality of this methodology was illustrated by performing the reaction on a gram-scale with the same efficiency and stereoselectivity.
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