1433963-94-0Relevant 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 (2012)
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
