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

Autor: Arun Prasath Lingam Kandapalam, Devarajan Kathirvelan, Huidrom Birkumar Singh, Sankaranarayanan Nagarajan, Panneerselvam Yuvaraj
Rok vydání: 2020
Předmět:
Zdroj: Journal of Chemical Sciences. 132
ISSN: 0973-7103
0974-3626
Popis: 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%.
Databáze: OpenAIRE
Externí odkaz: