The preparation of bicyclic pyrrolidines, stable and easy to isolate, is performed through both classical solution chemistry and on solid support. A new linker strategy is presented based on the concept of REM resin approach. Starting from a suitably derivatized Wang's resin, the linker can be REgenerated after cleavage of the product and functionalized to start a new synthetic cycle via a Michael reaction. In the present work a vinyl sulfone supported on a Wang's resin is able to undergo a Michael reaction with an amino acid derivative; the obtained adduct serves as a precursor for azomethine ylide generation, which is conveniently trapped with N-methyl-maleimide. The results are presented and discussed in the light of the experimental conditions applied as well as the method chosen for the cleavage of the product and resin regeneration.

Solid phase synthesis of bicyclic pyrrolidines

Quadrelli P.
Writing – Original Draft Preparation
2021

Abstract

The preparation of bicyclic pyrrolidines, stable and easy to isolate, is performed through both classical solution chemistry and on solid support. A new linker strategy is presented based on the concept of REM resin approach. Starting from a suitably derivatized Wang's resin, the linker can be REgenerated after cleavage of the product and functionalized to start a new synthetic cycle via a Michael reaction. In the present work a vinyl sulfone supported on a Wang's resin is able to undergo a Michael reaction with an amino acid derivative; the obtained adduct serves as a precursor for azomethine ylide generation, which is conveniently trapped with N-methyl-maleimide. The results are presented and discussed in the light of the experimental conditions applied as well as the method chosen for the cleavage of the product and resin regeneration.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11571/1445356
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 0
  • ???jsp.display-item.citation.isi??? ND
social impact