39696-82-7Relevant academic research and scientific papers
Enantioselective Construction of Single and Vicinal All-Carbon Quaternary Stereocenters through Ion-Pair-Catalyzed 1,6-Conjugate Addition
Zhu, Yasheng,Wang, Hongliang,Wang, Gang,Wang, Zehua,Liu, Zhaopeng,Liu, Lei
supporting information, p. 7248 - 7253 (2021/09/14)
An asymmetric 1,6-conjugate addition to presynthesized δ-aryl-δ-cyano-disubstituted para-quinone methides through bifunctional phosphonium-amide-promoted ion-pair catalysis for acyclic all-carbon quaternary stereocenter construction has been described. Both acyclic and cyclic 1,3-dicarbonyls participate in the asymmetric alkylation reaction, furnishing a wide array of diarylmethanes bearing a single acyclic quaternary carbon stereocenter or vicinal cyclic and acyclic quaternary carbon stereocenters with high efficiency and excellent stereoselectivity. Computational studies elucidate the origin of the enantioselectivity.
Synthesis of Chiral Triarylmethanes Bearing All-Carbon Quaternary Stereocenters: Catalytic Asymmetric Oxidative Cross-Coupling of 2,2-Diarylacetonitriles and (Hetero)arenes
Wang, Zehua,Zhu, Yasheng,Pan, Xiaoguang,Wang, Gang,Liu, Lei
, p. 3053 - 3057 (2020/02/05)
A direct and enantioselective oxidative cross-coupling of racemic 2,2-diarylacetonitriles with electron-rich (hetero)arenes has been described, which allows for efficient construction of triarylmethanes bearing all-carbon quaternary stereocenters with excellent chemo- and enantioselectivity. The reaction has an excellent functional group tolerance, and exhibits a broad scope with respect to both 2,2-diarylacetonitrile and (hetero)arene components. The rich chemistry of the cyano group allows for facile synthesis of other valuable chiral triarylmethanes bearing all-carbon quaternary centers that are otherwise difficult to access.
δ-Cyano substituted: Para -quinone methides enable access to unsymmetric tri- And tetraarylmethanes containing all-carbon quaternary stereocenters
Feng, Aili,Li, Wei,Liu, Lei,Qi, Yue,Sun, Shutao,Wang, Lin,Zhang, Fang,Zhu, Rongxiu
, p. 3522 - 3526 (2020/06/10)
para-Quinone methides bearing an electron-withdrawing cyano group at the exocyclic methylene δ-position were identified as valuable 1,6-conjugate addition building blocks for acyclic all-carbon quaternary stereocenter construction. A wide variety of electron-rich arenes as nucleophiles were tolerated, effectively furnishing diverse unsymmetrical triarylmethanes bearing all-carbon quaternary stereocenters. The robust transformable abilities of the cyano group provide a platform to access other valuable functional group-containing unsymmetrical tri- and tetraarylmethanes that are otherwise difficult to be prepared. Computational studies supported the hypothesis that the cyano group at the δ-position tunes the molecular electron-density distribution, and the stability of para-quinone methides is enhanced by lowering their polymerizability.
Accessing α-Arylated Nitriles via BF3·OEt2 Catalyzed Cyanation of para-Quinone Methides Using tert-Butyl Isocyanide as a Cyanide Source
Shirsath, Sachin R.,Shinde, Ganesh H.,Shaikh, Aslam C.,Muthukrishnan
, p. 12305 - 12314 (2018/10/02)
BF3·OEt2 catalyzed 1,6-conjugate addition of tert-butyl isocyanide to para-quinone methides and fuchsones for the synthesis of α-diaryl and α-triaryl nitriles has been reported. This protocol allows α-diaryl- and α-triaryl nitriles to be accessed in good to excellent yields and with a broad substrate scope, which could be further functionalized to give a versatile set of products. This is the first example wherein tert-butyl isocyanide has been used as a cyanide source for the 1,6-conjugate addition.
Phenyl-substituted normethadones: Synthesis and pharmacology
Mbela,Poupaert,Cumps,Moussebois,Haemers,Borloo,Dumont
, p. 237 - 242 (2007/10/02)
Phenyl-substituted normethadone derivatives were synthesized and their affinity (IC50) for opioid receptors was determined by displacement of the specific binding sites of [3H]sufentanyl on rat brain preparations. Substitution resulted in a decrease of affinity in-vitro. These results suggest that normethadone-like compounds may interact with the P subsite of the μ-opioid receptor and that the P subsite has a well-defined cavity shape of stringent dimensions.
