The effectiveness of a series of chiral phase transfer catalysts in cascade reactions of active methylene compounds with 2-cyanobenzaldehyde leading to chiral 3-substituted isoindolinones and fused benzoindolizidinones has been investigated. High yields and moderate enantiomeric excesses (e.e.s) were achieved employing a chiral phase-transfer catalyst derived from bifunctional urea–quinine. Moreover, an efficient process of heterochiral crystallization, performed on moderately enantioenriched compounds, led to an impressive increase of the enantiopurity up to 93% e.e.s.

Chiral phase transfer catalysts enable the synthesis of diverse chiral N-heterocycles through a combination of asymmetric cascade reactions

MASSA, Antonio
2015

Abstract

The effectiveness of a series of chiral phase transfer catalysts in cascade reactions of active methylene compounds with 2-cyanobenzaldehyde leading to chiral 3-substituted isoindolinones and fused benzoindolizidinones has been investigated. High yields and moderate enantiomeric excesses (e.e.s) were achieved employing a chiral phase-transfer catalyst derived from bifunctional urea–quinine. Moreover, an efficient process of heterochiral crystallization, performed on moderately enantioenriched compounds, led to an impressive increase of the enantiopurity up to 93% e.e.s.
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/11386/4650025
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 10
  • ???jsp.display-item.citation.isi??? 10
social impact