508216-81-7Relevant articles and documents
Highly enantioselective synthesis of 1,2,3-substituted cyclopropanes by using α-iodo- and α-chloromethylzinc carbenoids
Beaulieu, Louis-Philippe B.,Zimmer, Lucie E.,Gagnon, Alexandre,Charette, André B.
, p. 14784 - 14791 (2013/01/15)
Herein, we report the enantio- and diastereoselective formation of trans-iodo- and trans-chlorocyclopropanes from α-iodo- and α-chlorozinc carbenoids by using a dioxaborolane-derived chiral ligand. The synthetically useful iodocyclopropane building blocks were derivatized by an electrophilic trapping of the corresponding cyclopropyl lithium species or a Negishi coupling to give access to a variety of enantioenriched 1,2,3-substituted cyclopropanes. The synthetic utility of this method was demonstrated by the formal synthesis of an HIV-1 protease inhibitor. In addition, the related stereoselective bromocyclopropanation was also investigated. New insights about the relative electrophilicity of haloiodomethylzinc carbenoids are also presented. Propping up the enantioselectivity: The enantio- and diastereoselective formation of trans-iodo- and trans-chlorocyclopropanes from α-iodo- and α-chlorozinc carbenoids by using a dioxaborolane-derived chiral ligand is reported. The iodocyclopropanes were derivatized into a variety of 1,2,3-substituted cyclopropanes and new insights into the relative electrophilicity of α-haloiodomethylzinc carbenoids are presented (see scheme). Copyright
(2S,1′S,2′S,3′R)-2- (2′-carboxy-3′-methylcyclopropyl) glycine is a potent and selective metabotropic group 2 receptor agonist with anxiolytic properties
Collado, Iván,Pedregal, Concepción,Mazón, Angel,Espinosa, Juan Félix,Blanco-Urgoiti, Jaime,Schoepp, Darryle D.,Wright, Rebecca A.,Johnson, Bryan G.,Kingston, Ann E.
, p. 3619 - 3629 (2007/10/03)
The asymmetric synthesis and biological activity of (2S,1′S,2′S,3′R)-2- (2′-carboxy-3′-methylcyclopropyl) glycine 7 and its epimer at the C3′ center 6 are described. Compound 7 is a highly potent and selective agonist for group 2 metabotropric glutamate r
Synthesis and biological evaluation of novel 2-(1H-imidazol-4-yl)cyclopropane carboxylic acids: key intermediates for H3 histamine receptor ligands.
Brana, Miguel F,Guisado, Cristina,Fernando Alguacil, Luis,Garrido, Elisa,Perez-Garcia, Carmen,Ruiz-Gayo, Mariano
, p. 3561 - 3563 (2007/10/03)
A new synthetic methodology to provide cis-2-(1H-imidazol-4-yl)-cyclopropane carboxylic acids is described. These cyclopropanes are useful for the preparation of novel H(3) receptor agents.
