Search

Two strategies based on kinetic resolution(s) of chiral alanes and providing enantioenriched synhomoallylamines are reported. The first implies a single kinetic resolution of the alane using camphor; the second requires two sequential kinetic resolutions using the synergistic combination of (−)-camphor/(R)-tert-butylsulfinamide-derived imines. This synselectivity, specific to the use of allyaluminum, opens the way to the preparation of valuable building blocks as illustrated by the synthesis of (+)-epilupinamine.

Polyhydroxylated quinolizidines bearing a hydroxymethyl group at the ring junction were synthesized from a readily available l-sorbose-derived ketonitrone. Evaluated as glycoside hydrolase inhibitors, these quinolizidines revealed to be potent and selective α-glucosidase inhibitors. Quinolizidine 9ais the first quinolizidine-scaffolded iminosugar exhibiting nanomolar inhibition of a glycoenzyme.