Optically active γ-methyl-β-hydroxy and γ-alkoxy-β-hydroxy ketones have been obtained by condensing chiral racemic aldehydes with chiral α-sulphinyl hydrazones. Good to excellent enantioselectivity and diastereoselectivity, both strongly dependent on the nature of the substrates and the reaction conditions, were achieved. The absolute and relative configuration of some of the ketols have been established, and a model to account for the stereochemical outcome of this reaction is discussed.

Double stereoselection in the aldol-type synthesis of gamma-methyl and gamma- alkoxy-beta-hydroxyketones mediated by alpha-sulphinylhydrazones / R. Annunziata, S. Cardani, M. Cinquini, F. Cozzi, A. Gilardi, G. Poli, C. Scolastico. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - :2(1985), pp. 255-259.

Double stereoselection in the aldol-type synthesis of gamma-methyl and gamma- alkoxy-beta-hydroxyketones mediated by alpha-sulphinylhydrazones

R. Annunziata
Primo
;
M. Cinquini;F. Cozzi;
1985

Abstract

Optically active γ-methyl-β-hydroxy and γ-alkoxy-β-hydroxy ketones have been obtained by condensing chiral racemic aldehydes with chiral α-sulphinyl hydrazones. Good to excellent enantioselectivity and diastereoselectivity, both strongly dependent on the nature of the substrates and the reaction conditions, were achieved. The absolute and relative configuration of some of the ketols have been established, and a model to account for the stereochemical outcome of this reaction is discussed.
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

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/2434/185165
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 11
  • ???jsp.display-item.citation.isi??? 12
social impact