1202702-07-5Relevant academic research and scientific papers
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.
supporting information, 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
Enantio-and diastereoselective iodocyclopropanation of allylic alcohols by using a substituted zinc carbenoid
Beaulieu, Louis-Philippe B.,Zimmer, Lucie E.,Charette, Andr B.
supporting information; experimental part, p. 11829 - 11832 (2010/06/15)
The first enantioselective Simmons Smith iodocyclopropanation reaction, in which iodoform is used as the precursor to the substituted zinc carbenoid, was reported. The nature of the carbenoid was examined by quenching the preformed zinc carbenoid with Ds
