25628-96-0Relevant academic research and scientific papers
Diastereoselective α-Alkylation of Metallo Enamines Generated from N-C Axially Chiral Mebroqualone Derivatives
Matsuoka, Mizuki,Goto, Mitsuhiro,Wzorek, Alicja,Soloshonok, Vadim A.,Kitagawa, Osamu
, p. 2650 - 2653 (2017)
The reactions of various alkyl halides with the metallo enamines generated from racemic and optically pure N-C axially chiral mebroqualone derivatives were found to proceed with a synthetically attractive stereochemical outcome (up to 99% yield and up to dr = 26:1) allowing preparation of a structurally new type of pharmaceutically interesting compounds possessing elements of axial and central chirality.
α-Alkylation of N-C Axially Chiral Quinazolinone Derivatives Bearing Various ortho -Substituted Phenyl Groups: Relation between Diastereoselectivity and the ortho -Substituent
Matsuoka, Mizuki,Iida, Asumi,Kitagawa, Osamu
supporting information, p. 2126 - 2130 (2018/06/08)
2-Ethylquinazolin-4-one derivatives bearing various ortho -substituted phenyl groups were revealed to possess a stable C-N axially chiral structure at ambient temperature. The reactions of alkyl halides with the anionic species prepared from these quinazolinones were systematically explored. The α-alkylation reactions proceeded with diastereoselectivities ranging from 1:1 to >50:1, depending upon the steric bulk of the ortho -substituent, to afford products having the elements of axial and central chirality in high yields (85-98%).
