1476067-44-3Relevant academic research and scientific papers
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.).
α-isocupreine, an enantiocomplementary catalyst of β-isocupreidine
Nakamoto, Yoshito,Urabe, Fumiya,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi
supporting information, p. 12653 - 12656 (2013/10/01)
Complementary chemistry! α-Isocupreine (α-ICPN) was synthesized for the first time in one step from quinine by treatment with CF 3SO3H (see scheme). This compound serves as an enantiocomplementary catalyst to β-isocupreidine (β-ICD)
