Organocatalyzed enantioselective desymmetrization of aziridines and epoxides
نویسنده
چکیده
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.
منابع مشابه
Guanidine-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 کاملChiral Brønsted acid-catalyzed diastereo- and enantioselective synthesis of CF3-substituted aziridines.
A multicomponent organocatalyzed highly diastereo- and enantioselective synthesis of CF(3)-substituted aziridines is described. This reaction of in situ generated CF(3)CHN(2) and aldimines was realized by chiral Brønsted acid catalysis. The utility of the products is illustrated by easy access to β-CF(3) isocysteine and aziridine-containing dipeptides.
متن کاملLithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols
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.
متن کاملEnantioselective Ring-Opening
Ever since Nugent first reported a practical, catalytic method for the enantioselective opening of meso-epoxides with trimethylsilyl azide (TMSN3), [1] such desymmetrization reactions of epoxides and aziridines using a variety of nucleophiles have been the subject of extensive research. The less developed ring-opening reactions, those of meso-aziridines by carbon and nitrogen nucleophiles, give...
متن کاملWidening the usefulness of epoxides and aziridines in synthesis
Epoxides and aziridines are common intermediates in synthesis. Readily accessible in enantioenriched form, they are typically used as electrophiles, taking advantage of their predictable highly regioselective ring-opening reactions. Our work in the area of α-lithiated terminal epoxides and aziridines indicates that there are many other less conventional but useful reactions of these small-ring ...
متن کامل