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

Yuvaraj, Panneerselvam; Singh, Huidrom Birkumar; Kandapalam, Arun Prasath Lingam; Kathirvelan, Devarajan; Nagarajan, Sankaranarayanan

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. 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%.

Journal of Chemical Sciences, 2020, Vol 132, Issue 1, p1

0974-3626

Academic Journal

10.1007/s12039-020-01772-7