Chemoselective and diastereodivergent synthesis of new spirooxindolo-pyrrolizidines and pyrrolidines stemming from unsymmetrical 1,3-bis(arylidene)tetral-2-ones: a combined experimental and theoretical study

Abstract

Both theoretical and experimental study of a three-components one-pot cycloaddition reaction involving unstabilized azomethine ylides and unsymmetrical exocyclic dienones featuring a tetralone core was performed. Two new families of highly...

Decarboxylative 1,3-dipolar cycloadditions of l-proline

“…The Lamsabhi research team introduced the synthesis of a new class of spiro-oxindolopyrrolizidines and pyrrolidines through a four-component (3 + 2)-cyclization reaction ( Scheme 25 ). 64 In this regard, they treated isatins 2, and l -proline 1/ l -valine 83 with p -substituted 1,3-bis(arylidene)tetral-2-ones 82 in EtOH as a solvent. According to the results of DFT calculations, the authors realized that due to the higher reactivity of the double bond at the 3-position relative to the double bond at the 1-position in enone 82, the reaction proceeded with high chemoselectivity and two products 84 and 85 were detected with high diastereomeric excess.…”