Catalytic Enantioselective Construction of Chiral γ-Azido Nitriles through Nitrile Group-Promoted Electrophilic Reaction of Alkenes
Congratulations! The publication of our group in Org. Lett., "Catalytic Enantioselective Construction of Chiral γ-Azido Nitriles through Nitrile Group-Promoted Electrophilic Reaction of Alkenes" has been published recently (Yaoyu Liang #, Hongtai Huang #, Nan Huang #, Lihao Liao*, and Xiaodan Zhao* Org. Lett., 2023, 25, 6757-6762, # These authors contributed equally to this work).
An efficient approach for the construction of enantioenriched γ-azido nitriles through the chiral sulfide-catalyzed asymmetric electrophilic thioazidation of allylic nitriles is disclosed. A wide range of electron-deficient and -rich aryl, heterocyclic aryl, and alkyl substituents are suitable on the substrates of allylic nitriles. The regio-, enantio-, and diastereoselectivities of the reactions are excellent. As versatile platform molecules, the obtained chiral γ-azido nitriles can be easily converted into high-value-added chiral molecules that are not easily accessed by other methods. Control experiments revealed that the allylic nitrile group is important for control of the reactivity and enantioselectivity of the reaction leading to a broad substrate scope.
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