Regioselective copper-catalyzed alkylation of [2.2.2]-acylnitroso cycloadducts: remarkable effect of the halide of Grignard reagents.
Ring opening with organometallic reagents of [2.2.2]-acylnitroso cycloadducts, including an enantioselective kinetic resolution of these compounds, has been accomplished for the first time. By the careful choice of reaction conditions, it was possible to obtain new cyclohexenyl hydroxamic acids with complete anti-stereoselectivity and a nice regioalternating control. A remarkable effect of the halogen of the Grignard reagent was observed during ring opening.
Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Universita di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
Stefano
S
Crotti
Ferruccio
F
Bertolini
Valeria
V
di Bussolo
Mauro
M
Pineschi
D000478:Alkylation; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D009603:Nitroso Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007202:Indicators and Reagents; D009603:Nitroso Compounds; D003300:Copper