title: Enantioselective Oxidation of Alkenes with Potassium Permanganate Catalyzed by Chiral Dicationic Bisguanidinium.
abstract: Chiral anion-controlled ion-pairing catalysis was demonstrated to be a wide-ranging strategy that can utilize a variety of cationic metal species. In a similar manner, we envision a complementary strategy using chiral cation in partnership with inorganic anionic metal salts. Herein, we report a chiral dicationic bisguanidinium-catalyzed asymmetric oxidation reaction of alkenes with potassium permanganate. Chiral induction is attributed to ion-pairing interaction between chiral cation and enolate anion. The success of the current permanganate oxidation reaction together with mechanistic insights should provide inspiration for expansion to other anionic metal salts and would open up new paradigms for asymmetric transition metal catalysis, phase-transfer catalysis, and ion-pairing catalysis.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , 21 Nanyang Link, Singapore, Singapore 637371.
authors.forename: Chao
authors.initials: C
authors.lastname: Wang
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , 21 Nanyang Link, Singapore, Singapore 637371.
authors.forename: Lili
authors.initials: L
authors.lastname: Zong
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , 21 Nanyang Link, Singapore, Singapore 637371.
authors.forename: Choon-Hong
authors.initials: CH
authors.lastname: Tan
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D019791:Guanidine / Q000737:chemistry*; D010084:Oxidation-Reduction; D011196:Potassium Permanganate / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D011196:Potassium Permanganate; D019791:Guanidine