Michael addition of lithium enolates of g-butyrolactone 1 and a-methyl-g-butyrolactone 10 to (E)-1-nitropropene 2, (E)-bnitrostyrene 3 and (E)-2-nitro-1-phenylpropene 4 is described. Reactions of the lithium enolate of 10 with 2 and 4 occurred with high diasteroselectivity (80 and 92% d.e., respectively). Reactions of the zinc enolate of 10 with two b-nitroenamines and two methylthiosubstituted 1-amino-2-nitro-1,3-dienes were also examined. Catalytic reduction of the nitroalkylated and nitroalkenylated products allowed the achievement of functionalized g-lactams and/or cyclic hydroxamic acids.
Nitroalkylation and nitroalkenylation reactions of gamma-lactone enolates. A facile ring switch from polysubstituted gamma-lactones to polysubstituted gamma-lactams / Forzato, Cristina; Nitti, Patrizia; Pitacco, Giuliana; Valentin, Ennio; S., Morganti; E., Rizzato; D., Spinelli; C., Dell'Erba; G., Petrillo; C., Tavani. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 60:(2004), pp. 11011-11027. [10.1016/j.tet.2004.07.084]
Nitroalkylation and nitroalkenylation reactions of gamma-lactone enolates. A facile ring switch from polysubstituted gamma-lactones to polysubstituted gamma-lactams
FORZATO, Cristina;NITTI, PATRIZIA;PITACCO, GIULIANA;VALENTIN, ENNIO;
2004-01-01
Abstract
Michael addition of lithium enolates of g-butyrolactone 1 and a-methyl-g-butyrolactone 10 to (E)-1-nitropropene 2, (E)-bnitrostyrene 3 and (E)-2-nitro-1-phenylpropene 4 is described. Reactions of the lithium enolate of 10 with 2 and 4 occurred with high diasteroselectivity (80 and 92% d.e., respectively). Reactions of the zinc enolate of 10 with two b-nitroenamines and two methylthiosubstituted 1-amino-2-nitro-1,3-dienes were also examined. Catalytic reduction of the nitroalkylated and nitroalkenylated products allowed the achievement of functionalized g-lactams and/or cyclic hydroxamic acids.Pubblicazioni consigliate
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