对映选择性亲电氟化反应研究进展

Progresses in Enantioselective Electrophilic Fluorinations

含氟有机化合物,特别是手性氟化物在医药、农药及功能性材料等相关领域的作用备受注目.尽管在分子中有立体选择性地引入一个氟原子一直是有机化学家面临的一个挑战性问题,近年来在化学家们的不断努力下,对映选择性氟化反应研究取得重要进展.高光学活性的手性氟化物可通过手性亲电氟化试剂诱导的立体选择性氟化反应,基于底物的手性氟化反应以及手性催化剂诱导的不对称催化氟化反应等来制备.特别是,手性金属配合物和有机催化剂诱导的不对称催化氟化反应被广泛应用于各类手性氟化物的合成,已成为不对称氟化反应研究的热点.全面介绍对映选择性亲电氟化反应研究概况和最新进展,讨论各种不对称氟化反应的特点及应用范围.

Fluoroorganic compounds, especially chiral fluorinated compounds, are of importance in the pharmaceutical and agrochemical industries as well as in the development of functional materials and related areas. It has been a challenge for organic chemists to enantioselectively introduce a fluorine atom into one molecule. In recent years, enantioselective fluorinations have made significant progresses under chemists＇ continuous efforts. Chiral nonracemic fluoro-organic molecules with a fluorine atom on a stereogenic center are readily prepared via chiral electrophilic fluorinating reagent-mediated enantioselective fluorinations, substrate-controlled enantioselective electrophilic fluorinations, chiral metal complexes and asymmetric catalyst--directed catalytic enantioselective fluorinations. Especially, chiral metal complexes and organocatalysts in combination with electrophilic fluorinating reagents have found applications to the synthesis of a variety of chiral fluoroorganic compounds. This review will cover in detail the methods, strategies and recent developments in enantioselective electrophilic fluorinations, and discuss their applications and limitations of these asymmetric fluorination methods.