Regioselective copper-catalyzed alkylation of [2.2.2]-acylnitroso cycloadducts: remarkable effect of the halide of Grignard reagents

Stefano Crotti; Ferruccio Bertolini; Valeria di Bussolo; Mauro Pineschi

doi:10.1021/ol100454c

Regioselective copper-catalyzed alkylation of [2.2.2]-acylnitroso cycloadducts: remarkable effect of the halide of Grignard reagents

Org Lett. 2010 Apr 16;12(8):1828-30. doi: 10.1021/ol100454c.

Authors

Stefano Crotti¹, Ferruccio Bertolini, Valeria di Bussolo, Mauro Pineschi

Affiliation

¹ Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Universita di Pisa, Via Bonanno 33, 56126 Pisa, Italy.

PMID: 20232855
DOI: 10.1021/ol100454c

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Catalysis
Copper / chemistry*
Indicators and Reagents / chemistry
Nitroso Compounds / chemistry*
Stereoisomerism
Substrate Specificity

Substances

Indicators and Reagents
Nitroso Compounds
Copper