Highly efficient endo’- selective synthesis of (dispiro 3,2′-pyrrolidinyl) bisoxindoles containing three contiguous chiral stereocenters with two contiguous quaternary spirostereocenters

Abstract

An efficient, atom economical, one-pot synthesis of endo’- selective (dispiro 3,2′-pyrrolidinyl) bisoxindole containing three contiguous chiral stereocenters with two contiguous quaternary spirostereo centers have been achieved by three-component reaction of isatins, malononitrile (cyanoacetic ester) and 1,3-dicarbonyl compounds in water in the presence of L-proline. One-pot, azomethine ylide cycloaddition with a dipolarophile without using any catalyst have also been achieved in good yields. This new methodology offers many advantages of catalyst-free, mild reaction conditions, shorter reaction time, environmental friendliness, regio- and stereoselective processes in higher yields.

Graphic abstract

Synopsis: One-pot, azomethine ylide cycloaddition with a dipolarophile without using any catalyst provides endo’- selective (dispiro 3,2′-pyrrolidinyl) bisoxindole containing three contiguous chiral stereocenters with two contiguous quaternary spirostereo centers have been achieved in good yield. The reactions preceded under mild reaction conditions without any catalyst yields high regio- and stereoselective products up to 55–99%.

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Acknowledgements

The author PY thanks Science and Engineering Research Board (SERB) New Delhi Ref. No: EEQ/2017/000161 for financial support. The authors PY & HBS also grateful to the Director, CSIR-NEIST, Jorhat, Assam, India for his keen interest in this work.

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Correspondence to Panneerselvam Yuvaraj.

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Yuvaraj, P., Singh, H.B., Kandapalam, A.P.L. et al. Highly efficient endo’- selective synthesis of (dispiro 3,2′-pyrrolidinyl) bisoxindoles containing three contiguous chiral stereocenters with two contiguous quaternary spirostereocenters. J Chem Sci 132, 76 (2020). https://doi.org/10.1007/s12039-020-01772-7

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Keywords

  • 1,3-Dipolar cycloaddition
  • Endo-Selectivity
  • Dispiro-bis-oxindoles
  • HOMO-LUMO interaction