Iron catalyzed highly enantioselective cis-dihydroxylation of quinones

A method for asymmetric cis-dihydroxylation of a quinone comprising:

• (i) maintaining a reaction mixture at a temperature for a period of time sufficient to form a product,
• wherein the reaction mixture comprises the quinone, one or more iron-based catalyst(s), and a solvent,
• wherein the product comprises a cis-diol,
• wherein the one or more iron-based catalyst(s) have the structure of:
• or a stereoisomer thereof,
• wherein:
• (a) L1 is
• each occurrence of T′ is an unsubstituted C6 monocyclic group and p is 1;
• (b) R18 and R18′ are independently a substituted or unsubstituted C1-C6 alkyl;
• (c) R19 is an unsubstituted methylene:
• (d) R23 and R23′ are hydrogen;
• (e) R24 and R24′ are independently unsubstituted C1-C2 alkyl;
• (d) R25 and R25′ are independently a triflate or halide;
• and
• (e) the substituents, when present, are independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a carbonyl, a halide, a hydroxyl, an aroxy, an alkylthio, an arylthio, a cyano, an isocyano, an alkoxyl, a nitro, a carboxyl, an amino, an amido, an oxo, a silyl, a sulfinyl, a sulfonyl, a sulfonic acid, a phosphonium, a phosphanyl, a phosphoryl, a phosphonyl, or a thiol, or a combination thereof;
• and
• wherein the cis-diol has an enantiomeric excess from about 80% to 100%, as determined by chiral HPLC.