927808-35-3Relevant academic research and scientific papers
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.
The metal tin promoted cascade reaction of ketones in aqueous media for the construction of 2-bromo-4-aryl-1,3-pentadiene
Liu, Lingyan,Zhang, Yan,Zhang, Hua,Huang, Kaimeng,Gao, Bo-Xin,Zou, Min,Zhou, Xin,Wang, Hongkai,Li, Jing
, p. 5393 - 5399 (2014/07/21)
A novel type of transformation was discovered serendipitously during the Barbier-type allenylation reaction of aromatic ketones promoted by the metal, tin, in aqueous media. Additionally, a series of new, highly functionalized 2-bromo-4-aryl-1,3-pentadienes could be obtained with good yields in this reaction. This cascade reaction shows the unique properties of the metal, tin. Furthermore, it is actually a cascade reaction which involves two steps: one is the Barbier-type allenylation of the carbonyl compound, and the other is an SN2′ type addition-elimination reaction. Notably, this reaction has the advantages of simple, mild conditions and is easy to operate. Furthermore, the corresponding product could be applied to various coupling reactions or other diversified transformations. This journal is the Partner Organisations 2014.
Construction of highly substituted stereodefined dienes by cross-coupling of α-allenic acetates
Schneekloth Jr., John S.,Pucheault, Mathieu,Crews, Craig M.
, p. 40 - 43 (2007/10/03)
The assembly of highly substituted dienes remains a challenge for organic chemistry. This work represents a strategy for the construction of highly substituted 1,3-dienes by means of a Tsuji-Trost cross coupling between α-allenic acetates and organozinc reagents. The reaction is high yielding, and installs a trisubstituted olefin with E/Z selectivities up to 95:5 favoring the (E) product. A cheap, commercially available palladium precatalyst and a ligand are used to control the E/Z selectivity. Furthermore, an interesting reversal in selectivity is noted in which appropriate choice of ligand may be used to control the outcome of the reaction and favor the (Z) product. Thirteen examples are described, highlighting the substrate scope of the reaction. It is hoped that the straight-forward reaction conditions and high selectivity will make this reaction of broad use in natural product chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
