328564-56-3Relevant articles and documents
Ortho-Metalated dirhodium(II)-catalyzed α-diazocarbonyl transformation. Diastereoselective cyclopropanation of menthyl-α-diazo-β-keto ester and C-H insertion of α-diazo ester
Lahuerta, Pascual,Pereira, Inés,Pérez-Prieto, Julia,Sanaú, Mercedes,Stiriba, Salah-Eddine,Taber, Douglass F.
, p. 36 - 45 (2000)
ortho-Metalated rhodium(II) compound (1d1) containing two metalated P(C6H5)2(C6F5) and two acetates has successfully catalyzed cyclopropanation of menthyl-2-diazo-3-oxo-6-heptanoate (4) to form cyclopropanes 6 and 7 with significant cis-trans (30:70) diastereoselectivity. An enhanced performance of methyl-2-diazoundecanoate (5) cyclization has been achieved mediated by 2d1 and 2d4 catalysts, obtaining 71 and 85%, respectively, of the 1,5-C-H insertion product, trans-2-pentylcyclopentanecarboxylate (8) versus 1,2-elimination product, (Z)-2-undecenoate (9) (29 and 15%, respectively). The three possible diastereomers of catalyst (1d) which possess two ortho-metalated P(C6H5)2(C6F5) ligands in a head-to-tail configuration, with the two pentafluorophenyl groups in an endo-endo, endo-exo or exo-exo disposition have been separated by standard column chromatography. The X-ray structure analysis for two of these isomers 1d3endo-exo and 1d1endo-endo allows their structural assignment.