Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols
نویسندگان
چکیده
A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aromatic thiol nucleophiles. The resulting β-hydroxyl sulfides are obtained in excellent yield and enantioselectivity.
منابع مشابه
Organocatalyzed enantioselective desymmetrization of aziridines and epoxides
Enantioselective desymmetrization of meso-aziridines and meso-epoxides with various nucleophiles by organocatalysis has emerged as a cutting-edge approach in recent years. This review summarizes the origin and recent developments of enantioselective desymmetrization of meso-aziridines and meso-epoxides in the presence of organocatalysts.
متن کاملGuanidine-catalyzed enantioselective desymmetrization of meso-aziridines.
An amino-indanol derived chiral guanidine was developed as an efficient Brønsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities.
متن کاملHighly enantioselective iron(II)-catalyzed opening reaction of aromatic meso-epoxides with indoles.
A highly enantioselective method for the catalytic cis-stilbene oxide opening reaction with indole derivatives was developed. The scope of the reaction was studied with a selection of aromatic meso-epoxides and various indoles, and the desired 2-(indol-3-yl)ethanol derivatives were obtained in good to excellent yields with excellent enantioselectivities (from 96 to >99% ee).
متن کاملEpoxidation of Alkenes and Oxidation of Alcohols with Hydrogen Peroxide Catalyzed by a Fe (Br8TPPS) Supported on Amberlite IRA-400
Iron (III) meso-tetrakis(p-sulfonatophenyl)-β-octabromoporphyrin supported on Amberlite IRA- 400 [Fe(Br8 TPPS)-Ad-400] is a robust and efficient catalyst for oxidation of alkenes and alcohols at room temperature. The catalyst exhibits a high activity and stability in hydrocarbon oxidation by H2 O2 . The method was useful in the oxidation of various primary, secondary-aliphatic, alicyclic and ar...
متن کاملIron(II)-catalyzed enantioselective meso-epoxide-opening with anilines.
A highly enantioselective method for the catalytic opening of aromatic meso-epoxides with aniline derivatives was developed. The desired chiral β-amino alcohols were obtained in mostly good to very good yields with excellent enantioselectivities. Structural evidence of the pre-catalyst revealed a scarcely disclosed heptadentate Fe(II) complex with the chiral bipyridine ligand.
متن کامل