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Article Abstract

The first diastereo- and enantiodivergent asymmetric synthesis of new bis-spirocyclopropyloxindole scaffolds has been accomplished from the readily available isatin as a single starting material. Four -(1,2,3), -(1,2,3), rel-(1,2,3), and -(1,2,3) configurations of desired products were constructed in excellent enantiopurity via a simple switch in substrates using the chiral auxiliary-controlled method. The absolute configuration of cycloadducts with three contiguous quaternary/tertiary stereogenic centers was confirmed through X-ray diffraction analysis. A facile synthesis of versatile precursor 3-chlorooxindoles was also introduced.

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http://dx.doi.org/10.1021/acs.joc.2c02452DOI Listing

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