14050-94-3Relevant academic research and scientific papers
β-Isocupreidine-hexafluoroisopropyl acrylate method for asymmetric Baylis-Hillman reactions
Nakano, Ayako,Kawahara, Sakie,Akamatsu, Saori,Morokuma, Kenji,Nakatani, Mari,Iwabuchi, Yoshiharu,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi
, p. 381 - 389 (2006)
Key features of the β-isocupreidine (β-ICD)-catalyzed asymmetric Baylis-Hillman reaction of aldehydes with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) are presented. In addition, an improved method using azeotropically dried β-ICD is described.
Enantioselective Ammonium Ylide Mediated One-Pot Synthesis of Highly Substituted γ-Butyrolactones
Drennhaus, Till,?hler, Laura,Djalali, Saveh,H?fmann, Svenja,Müller, Clemens,Pietruszka, J?rg,Worgull, Dennis
supporting information, p. 2385 - 2396 (2020/04/30)
An ammonium ylide mediated access towards trans-β,γ-disubstituted, all-trans-α,β,γ-trisubstituted, and α,α,β,γ-tetrasubstituted γ-butyrolactones bearing a broad variety of functionalities was developed. Starting from widely accessible benzylidene Meldrum's acid derivatives and α-bromo carbonyl compounds, γ-butyrolactones were obtained in yields between 32–99% with up to excellent diastereoselectivities (>95:5) via a DABCO-mediated [2+1] annulation. Utilization of enantiomerically pure cinchona alkaloid derivatives enables the first asymmetric ammonium ylide mediated method to provide (3R,?4R)-β,γ-disubstituted and (2R,?3R,?4R)-α,β,γ-trisubstituted γ-butyrolactones in moderate to good yields with up to very good enantiomeric ratios (97:3). The scalability of the transformation was proven while determining the absolute configuration. (Figure presented.).
Asymmetric synthesis of natural product inspired tricyclic benzopyrones by an organocatalyzed annulation reaction
Waldmann, Herbert,Khedkar, Vivek,Dueckert, Heiko,Schuermann, Markus,Oppel, Iris M.,Kumar, Kamal
supporting information; experimental part, p. 6869 - 6872 (2009/04/06)
(Chemical Equation Presented) Going back to nature: Electron-deficient oxadienes and electron-poor acetylene carboxylates react in the presence of an organocatalyst to give natural product inspired tricyclic benzopyrones efficiently (up to 99% yield) and
