A stereoselective synthesis of (1R,2R,5S)-2-benzyloxymethyl-3-azabicyclo[3.2.0]heptane-2-one was achieved, by intramolecular [2+2]-cycloaddition of (R)-vinylglycinol-derived N-allyl-beta-N-keteniminium salts, with high facial diastereoselection. The regio- and stereochemical courses have been qualitatively investigated by Molecular Mechanics calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.

Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0] eptan-2-ones by [2+2]-cycloaddition of N-allyl beya-N-keteniminium salts derived from (R)-vinylglycinol / G., DELLE MONACHE; Misiti, Domenico; P., Salvatore; G., Zappia; Pierini, Marco. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 11:(2000), pp. 2653-2659. [10.1016/S0957-4166(00)00237-8]

Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0] eptan-2-ones by [2+2]-cycloaddition of N-allyl beya-N-keteniminium salts derived from (R)-vinylglycinol

MISITI, Domenico;PIERINI, MARCO
2000

Abstract

A stereoselective synthesis of (1R,2R,5S)-2-benzyloxymethyl-3-azabicyclo[3.2.0]heptane-2-one was achieved, by intramolecular [2+2]-cycloaddition of (R)-vinylglycinol-derived N-allyl-beta-N-keteniminium salts, with high facial diastereoselection. The regio- and stereochemical courses have been qualitatively investigated by Molecular Mechanics calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.
2000
01 Pubblicazione su rivista::01a Articolo in rivista
Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0] eptan-2-ones by [2+2]-cycloaddition of N-allyl beya-N-keteniminium salts derived from (R)-vinylglycinol / G., DELLE MONACHE; Misiti, Domenico; P., Salvatore; G., Zappia; Pierini, Marco. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 11:(2000), pp. 2653-2659. [10.1016/S0957-4166(00)00237-8]
File allegati a 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: https://hdl.handle.net/11573/255580
 Attenzione

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

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 14
  • ???jsp.display-item.citation.isi??? 12
social impact