Journal
ORGANIC LETTERS
Volume 20, Issue 4, Pages 909-912Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03667
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Funding
- Sichuan Youth Science and Technology Foundation [2015JQ0041, 2016JQ0024]
- Start-up Fund of Chengdu University [2081916044]
- National NSFC [21372217, 21572223, 21572224]
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Enantioselective dearomative [3 + 2] cycloaddition reaction of 2-nitrobenzofurans with 3-isothiocyanato oxindoles was developed. The reaction employs a chiral bis(oxazoline)/Zn(OTf)(2) catalyst, allowing a practical, straightforward access to structurally diverse spirooxindoles containing a 2,3-dihydrobenzofuran motif and three contiguous stereo-centers with excellent diastereo- and enantioselectivities. The synthetic potentials of the method have been demonstrated by the scale-up experiment and transformations of the products. The preliminary mechanism was investigated with experimental observations, nonlinear effects studies, and MS experiments.
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