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Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three‐Membered Carbocycles
Author(s) -
Zhang ZhiQi,
Zheng MengMeng,
Xue XiaoSong,
Marek Ilan,
Zhang FaGuang,
Ma JunAn
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201911701
Subject(s) - enantioselective synthesis , reagent , catalysis , yield (engineering) , chemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
Herein we described an efficient Rh II ‐catalyzed enantioselective cyclopropenation reaction of internal alkynes with a masked difluorodiazoethane reagent (PhSO 2 CF 2 CHN 2 , Ps‐DFA). This asymmetric transformation offers efficient access to a broad range of enantioenriched difluoromethylated cyclopropenes (40 examples, up to 99 % yield, 97 % ee ). The synthetic utility of obtained strained carbocycles is demonstrated by subsequent stereodefined processes, including cross‐couplings, hydrogenation, Diels–Alder reaction, and Pauson–Khand reaction.