Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three‐Membered Carbocycles | Zendy

Zhang ZhiQi | Zendy; Zheng MengMeng | Zendy; Xue XiaoSong | Zendy; Marek Ilan | Zendy; Zhang FaGuang | Zendy; Ma JunAn | Zendy

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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.

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