Journal
ORGANIC LETTERS
Volume 17, Issue 20, Pages 5020-5023Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02489
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Funding
- NSFC [21372217]
- Sichuan Youth Science and Technology Foundation [2013JQ0021, 2015JQ0041]
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A catalytic asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles and 3-nitroindoles has been disclosed with a chiral Zn(OTf)(2)/diphenylamine-linked bis(oxazoline) complex as the catalyst. A range of enantioenriched polycyclic spirooxindole derivatives containing three contiguous stereocenters were efficiently constructed in quantitative yields with excellent diastereo- and enantioselectivities. Importantly, the metal catalytic strategy in this work is significantly superior to the previous organocatalytic method in the diastereo- and enantioselectivities for almost all of the examined cases.
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