Asymmetric Catalytic Halofunctionalization of alpha,beta-Unsaturated Carbonyl Compounds

作者：Cai, Yunfei; Liu, Xiaohua; Zhou, Pengfei; Feng, Xiaoming^*

来源：Journal of Organic Chemistry, 2019, 84(1): 1-13.

DOI：10.1021/acs.joc.8b01951

• HIGHLY EFFICIENT SYNTHESIS
• ENANTIOSELECTIVE BROMOAMINOCYCLIZATION
• STEREOSELECTIVE AMINOBROMINATION
• AMINOHALOGENATION REACTION
• CONJUGATE ADDITION
• INTERMOLECULAR HALOETHERIFICATION
• SELECTIVE BROMOCYCLIZATION
• NEIGHBORING GROUPS
• ACID-DERIVATIVES
• OLEFINS

Halofunctionalization methods enable the vicinal difunctionalization of alkenes with heteroatom nucleophiles and halogen moieties. As a fundamental transformation in organic synthesis, the catalytic asymmetric variants have only recently been reported. In sharp contrast to the asymmetric halocyclization of simple alkenes which involves a nucleophile-assisted alkene activation process, the asymmetric halofunctionalization of enones developed by our laboratory features an electrophile-assisted 1,4-addition pathway. Our work in this area has resulted in the development of several different types of regio-, diastereo-, and enantioselective processes, including inter- and intramolecular haloaminations, haloetherifications, and haloazidations. The scope, updated mechanism, limitations, and future perspective of these reactions are discussed.

• 出版日期2019-1-4
• 单位四川大学; 重庆大学