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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Umpolung Strategy for the Synthesis of Chiral Dispiro[2-amino-4,5-dihydrofuran-3-carbonitrile]bisoxindoles
Li-Jun Chen1, Jin-Hang Yu1, Bin He1
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, P. R. China.
Abstract:
Based on a novel umpolung strategy, an efficient and highly enantioselective cascade aldol/cyclization/tautomerization of the 2-(2-oxoindolin-3-yl)malononitrile to active carbonyl compounds with excellent diastereo- and enantioselectivity has been developed. Also, various enantio-enriched multifunctional dispiro[2-amino-4,5-dihydrofuran-3-carbonitrile]bisoxindoles with adjacent spiro-stereocenters were conveniently obtained by this novel methodology. Also, the dispiro[2-amino-4,5-dihydrofuran-3-carbonitrile]bisoxindoles were easily transformed into structurally complex molecules without any effect on the diastereo- and enantioselectivity.
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