High enantiocontrol in the intramolecular cyclopropanation of diazo ketones catalyzed by dirhodium(II) complexes with ortho-metalated aryl phosphine ligands

M Barberis; J Pérez-Prieto; S E Stiriba; P Lahuerta

doi:10.1021/ol010170w

High enantiocontrol in the intramolecular cyclopropanation of diazo ketones catalyzed by dirhodium(II) complexes with ortho-metalated aryl phosphine ligands

Org Lett. 2001 Oct 18;3(21):3317-9. doi: 10.1021/ol010170w.

Authors

M Barberis¹, J Pérez-Prieto, S E Stiriba, P Lahuerta

Affiliation

¹ Departamento de Química Orgánica/Instituto de Ciencia Molecular, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot, Valencia.

PMID: 11594823
DOI: 10.1021/ol010170w

Abstract

[reaction: see text]. Chiral dirhodium(II) complexes, Rh2(O2CCF3)2(PC)2, [PCH = (p-CH3C6H4)3P, (m-CH3C6H4)3P], provide an excellent yield and a high enantiocontrol in the cyclopropanation of alpha-diazo ketones with gamma and delta double bonds. The ee values are significantly dependent on the solvent used; the best results are obtained using pentane.