Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 18, Pages 6243-6247Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600735
Keywords
asymmetric catalysis; aziridines; organic chemistry; palladium; spirooxindole
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Funding
- Natural Science Foundation of China [21232003, 21572074]
- Foundation for the Author of National Excellent Doctoral Dissertation of China (FANEDD) [201422]
- Outstanding Youth Funding in Hubei Province [2015CFA033]
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A catalytic asymmetric [3+ 2] cycloaddition reaction of chiral palladium-containing N-1-1,3-dipoles with methyleneindolinones has been successfully developed. The reaction allows an efficient construction of 3,3'-pyrrolinyl spirooxindoles with high yields and excellent stereoselectivities (up to 93% yield, 19:1 d.r. and >99% ee). A synthetic application of this methodology is demonstrated and a stereocontrol mechanism is proposed.
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