6109-33-7Relevant academic research and scientific papers
Metal-Free Formal Oxidative C?C Coupling by In Situ Generation of an Enolonium Species
Kaiser, Daniel,de la Torre, Aurélien,Shaaban, Saad,Maulide, Nuno
, p. 5921 - 5925 (2017/05/12)
Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so-called “natural”, polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well-known strategy, polarity reversal at the α-position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal-free oxidative C?C coupling.
A new chemoenzymatic approach to the synthesis of chiral 4-aryl-1,4-dihydro-2H-isoquinolines via the enzymatic resolution of 2-acetyl-4-phenyl-1,4-dihydro-2H-isoquinolin-3-one
Koszelewski, Dominik,Cwiklak, Malgorzata,Ostaszewski, Ryszard
, p. 1256 - 1261 (2012/11/07)
A new chemoenzymatic method is proposed for the synthesis of enantiomerically pure 4-phenyl-1,4-dihydro-2H-isoquinolines based on the enzymatic kinetic resolution of 2-acetyl-4-phenyl-1,4-dihydro-2H-isoquinolin-3- one. For the enzymatic resolution of the racemic substrate, readily available 'home made' animal liver acetone powders (LAPs) were used. Excellent enantioselectivity, exceeding 500, was achieved in a short reaction time upon application of turkey liver acetone powder as the biocatalyst. Reduction of obtained product led to the formation of amine (R)-1, which is hardly available using standard procedures. These results show that N-acetyl lactams are a new type of substrate for enzymatic biotransformations.
A Convenient Synthetic Route to 4-Aryl-1,4-dihydro-3(2H)-isoquinolinones
Petrov, Orlin S.,Ognyanov, Vassil I.,Mollov, Nikola M.
, p. 637 - 638 (2007/10/02)
The title compounds are synthesized by Friedel-Crafts cyclization of N-benzyl-α-chloroacetamides, derived from the dichlorocarbene adducts of benzaldehyde N-benzylimines.
