The double addition of organometallic reagents to fused oxazino-oxazines prepared from glyoxal and (S)-phenylglycinol afforded C2- or C1-symmetric 1,2-ethylenebis(-aminoalcohols), depending on the nature of the organometallic reagent. This route was modified by the use of (S)-valinol and phenylglyoxal as starting materials, and by reduction of the oxazino-oxazines by diborane. Cyclization of the -aminoalcohol moieties gave 1,2-ethylenediaziridines bearing one substituent/stereocenter on the ring carbon and one, two or no substituents/stereocenters in the ethylene tether. These bis(aziridines) were used as ligands in the Pd-catalyzed allylic alkylation of dimethyl malonate. It was established that the substituent(s) in the carbon tether and the configuration of the corresponding stereocenters have limited influence on the enantioselectivity.

Stereoselective Synthesis of Substituted 1,2-Ethylenediaziridines and Their Use as Ligands in Palladium-Catalyzed Asymmetric Allylic Alkylation / A. Gualandi; F. Manoni; M. Monari; D. Savoia. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 66:(2010), pp. 715-720. [10.1016/j.tet.2009.11.062]

Stereoselective Synthesis of Substituted 1,2-Ethylenediaziridines and Their Use as Ligands in Palladium-Catalyzed Asymmetric Allylic Alkylation

GUALANDI, ANDREA;MONARI, MAGDA;SAVOIA, DIEGO
2010

Abstract

The double addition of organometallic reagents to fused oxazino-oxazines prepared from glyoxal and (S)-phenylglycinol afforded C2- or C1-symmetric 1,2-ethylenebis(-aminoalcohols), depending on the nature of the organometallic reagent. This route was modified by the use of (S)-valinol and phenylglyoxal as starting materials, and by reduction of the oxazino-oxazines by diborane. Cyclization of the -aminoalcohol moieties gave 1,2-ethylenediaziridines bearing one substituent/stereocenter on the ring carbon and one, two or no substituents/stereocenters in the ethylene tether. These bis(aziridines) were used as ligands in the Pd-catalyzed allylic alkylation of dimethyl malonate. It was established that the substituent(s) in the carbon tether and the configuration of the corresponding stereocenters have limited influence on the enantioselectivity.
2010
Stereoselective Synthesis of Substituted 1,2-Ethylenediaziridines and Their Use as Ligands in Palladium-Catalyzed Asymmetric Allylic Alkylation / A. Gualandi; F. Manoni; M. Monari; D. Savoia. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 66:(2010), pp. 715-720. [10.1016/j.tet.2009.11.062]
A. Gualandi; F. Manoni; M. Monari; D. Savoia
File in questo prodotto:
Eventuali allegati, non sono esposti

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: https://hdl.handle.net/11585/89025
 Attenzione

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

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 12
  • ???jsp.display-item.citation.isi??? 12
social impact