78808-38-5Relevant articles and documents
Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations
Petrone, David A.,Isomura, Mayuko,Franzoni, Ivan,R?ssler, Simon L.,Carreira, Erick M.
, p. 4697 - 4704 (2018)
An enantioconvergent C(sp3)-C(sp3) coupling between racemic allenylic electrophiles and alkylzinc reagents has been developed. An Ir/(phosphoramidite,olefin) catalyst provides access to highly enantioenriched allenylic substitution p
Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate
Yamashita, Yasuhiro,Cui, Yi,Xie, Peizhong,Kobayashi, Shu
supporting information, p. 6042 - 6045 (2016/01/09)
Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.
Efficient synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl- 5,6-dihydropyran-2-ones via the PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols
Cheng, Xin,Jiang, Xuefeng,Yu, Yihua,Ma, Shengming
supporting information; experimental part, p. 8960 - 8965 (2009/04/11)
(Chemical Equation Presented) A mild and efficient methodology involving PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols with CuCl2 for the synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl-5,6-dihydropyran-2-ones was developed. This reaction proceeded in a highly regioselective manner, i.e., the chlorine atom was introduced to the terminal position of the allene moiety while the lactone linkage was formed between the center carbon atom of the allene moiety and the hydroxyl oxygen, which was established by the X-ray single crystal diffraction study of γ-lactone 3p. The highly optically active 3-chloromethyl-2(5H)-furanones could be easily prepared from the readily available optically active 2,3-allenols. A mechanism for this reaction was proposed.
