Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three-Membered Carbocycles.

Zhang, Zhi-Qi; Zheng, Meng-Meng; Xue, Xiao-Song; Marek, Ilan; Zhang, Fa-Guang; Ma, Jun-An

Zhang, Zhi-Qi; Zheng, Meng-Meng; Xue, Xiao-Song; Marek, Ilan; Zhang, Fa-Guang; Ma, Jun-An.

Afiliación

Zhang ZQ; Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin, 300072, P. R. China.
Zheng MM; Joint School of NUS & TJU, International Campus of Tianjin University, Fuzhou, 350207, P. R. China.
Xue XS; State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, P. R. China.
Marek I; State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, P. R. China.
Zhang FG; Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, 3200009, Israel.
Ma JA; Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin, 300072, P. R. China.

Angew Chem Int Ed Engl ; 58(50): 18191-18196, 2019 Dec 09.

Article en En | MEDLINE | ID: mdl-31633856

RESUMEN

Herein we described an efficient RhII -catalyzed enantioselective cyclopropenation reaction of internal alkynes with a masked difluorodiazoethane reagent (PhSO2 CF2 CHN2 , 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.

Palabras clave

cyclopropenation; diazo compounds; homogeneous catalysis; internal alkynes; metal carbenes

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