Organocatalytic Route to Dihydrocoumarins and Dihydroquinolinones
in All Stereochemical Configurations
- Publication date
- Publisher
Abstract
A straightforward
stereodivergent route to dihydrocoumarins and
dihydroquinolinones based on cinchona alkaloid catalyzed addition
reactions of monothiomalonates (MTMs) to functionalized nitroolefins
followed by deprotection and chemoselective cyclization has been developed.
The synthesis proceeds under mild conditions and yields heterocycles
with adjacent quaternary and tertiary stereogenic centers in very
high yields and stereoselectivities. Moreover, full control over the
relative and absolute configuration is achieved by the use of (pseudo)enantiomeric
catalysts and the difference in reactivity of thioester versus oxoester
moieties