657404-54-1Relevant academic research and scientific papers
Asymmetric Dearomatization of the Furan Ring Promoted by Conjugate Organolithium Addition to (Menthyloxy)(3-furyl)carbene Complexes of Chromium
Barluenga, Jose,Nandy, Sandip K.,Santosh Laxmi,Suarez, Jose Ramon,Merino, Isabel,Florez, Josefa,Garcia-Granda, Santiago,Montejo-Bernardo, Jose
, p. 5725 - 5736 (2003)
The sequential low-temperature addition reaction of an organolithium compound and methyl triflate to (menthyloxy)(3-furyl)carbene complexes of chromium and tungsten proceeded with excellent regioselectivity (1,4-addition) and diastereoselectivity (2,3-trans disposition of the nucleophile and electrophile groups) to afford new 2,3-disubstituted (2,3-dihydro-3-furyl)-carbene complexes. In addition, a high degree of diastereofacial selectivity was achieved by employing alkenyllithium compounds. After detachment of both the metal fragment and the chiral auxiliary group, trisubstituted 2,3-dihydrofuran derivatives containing a quaternary stereogenic center at the C3 position were obtained. The characterization, including X-ray crystallography, of a novel type of stable four-membered chelate (η 2-alkene)tetracarbonyl-carbene complex of chromium is also reported.
