Catalytic asymmetric alkylation of substituted isoflavanones.

ABSTRACT: The asymmetric alkylation of isoflavanones (3-aryl-chroman-4-ones) and protected 3-phenyl-2,3-dihydroquinolin-4(1H)-ones catalyzed by a novel cinchonidine-derived phase transfer catalyst E is reported. This functionalization occurs at the unactivated C3 methine to afford novel products that can easily be functionalized to generate more complex fused ring systems. The process accommodates a variety of isoflavanones and activated electrophiles and installs a stereogenic quaternary center in high yield and with good-to-excellent selectivity. Isoflavanones are a privileged class of natural products with a broad spectrum of biological activities including insecticidal, antimicrobial, antibacterial, estrogenic, antitumor, and anti-HIV activity. (1) Isoflavanones are also precursors for more comp

SUBMITTER: Nibbs AE 

PROVIDER: S-EPMC2733932 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature