Catalytic Enantioselective Construction of Chiral γ-Azido Nitriles through Nitrile Group-Promoted Electrophilic Reaction of Alkenes

• DOI: 10.1021/acs.orglett.3c02650
• Publication Date: 2023-09-01T19:25:32Z
• Authors: Yaoyu Liang; Hongtai Huang; Nan Huang; Lihao Liao; Xiaodan Zhao
• Keywords: Functional group; Reactivity

An efficient approach for the construction of enantioenriched γ-azido nitriles through chiral sulfide-catalyzed asymmetric electrophilic thioazidation allylic is disclosed. A wide range electron-deficient and -rich aryl, heterocyclic alkyl substituents are suitable on substrates nitriles. The regio-, enantio-, diastereoselectivities reactions excellent. As versatile platform molecules, obtained can be easily converted into high-value-added molecules that not accessed by other methods. Control experiments revealed nitrile group important control reactivity enantioselectivity reaction leading to a broad substrate scope.