64262-65-3Relevant academic research and scientific papers
A facile and convenient synthesis of trisubstituted (E)-α,β-unsaturated esters by tandem acetylation-E1CB reaction
Ozeki, Minoru,Hachino, Ayumi,Shigeta, Takashi,Niki, Aya,Kobayashi, Natsuko,Mizutani, Hideki,Nakamura, Akihiro,Horie, Ayano,Arimitsu, Kenji,Kajimoto, Tetsuya,Hosoi, Shinzo,Iwasaki, Hiroki,Kojima, Naoto,Yamashita, Masayuki,Kawasaki, Ikuo
, p. 71 - 74 (2019/01/17)
A facile and convenient synthesis of trisubstituted (E)-α,β-unsaturated esters was developed by improving our previously established method. The new method circumvented the separation of the intermediates, which have an activating group of the hydroxyl group in β-hydroxy esters, furnishing α,β-unsaturated esters in shorter steps than the previous method: an acetylation of β-hydroxy group and subsequent E1cB reaction proceeded in tandem. In addition, the new method can not only employ a diastereomeric mixture of the substrate for the E1cB reaction, it has a wide substrate scope as well, which would enable the synthesis of various trisubstituted (E)-α,β-unsaturated esters.
Mapping the mechanism of nickel-ferrophite catalysed methylation of baylis-hillman-derived SN2′ electrophiles
Novak, Andrew,Calhorda, Maria Jose,Costa, Paulo Jorge,Woodward, Simon
experimental part, p. 898 - 903 (2009/07/19)
Enantioselective Ni-catalysed methylation of Baylis-Hillman-derived allylic electrophiles in the presence of ferrophite ligands has been investigated computationally and experimentally. The sense and degree of enantioselectivity attained is independent of both the leaving group and the isomeric structure of the initial allylic halide. DFT studies support the selective formation of a limited number of energetically favoured anti and syn π-allyl intermediates. The observed regio- and enantioselectivity can be rationalised based on the energetics of these structures.
