Acetic acid promoted tandem cyclization of in situ generated 1,3-dipoles: stereoselective synthesis of dispiroimidazolidinyl and dispiropyrrolidinyl oxindoles with multiple chiral stereocenters†,10.1039/C5RA17215B

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Acetic acid promoted tandem cyclization of in situ generated 1,3-dipoles: stereoselective synthesis of dispiroimidazolidinyl and dispiropyrrolidinyl oxindoles with multiple chiral stereocenters†

Koorathota Suman,Sathiah Thennarasu

RSC Advances Pub Date : 09/11/2015 00:00:00 , DOI:10.1039/C5RA17215B

Abstract

We report acetic acid promoted in situ generation of ketimine and a 1,3-dipole that results in regio- and diastereoselective formation of dispiropyrrolidineoxindoles and dispiroimidazolidineoxindoles via tandem cycloaddition. This novel one-pot reaction generates four chiral centres with two contiguous spirostereocenters in dispiropyrrolidineoxindoles, and three chiral centres with two distal spirostereocenters in dispiroimidazolidineoxindoles.