Two-step stereocontrolled synthesis of densely functionalized cyclic beta-aminoesters containing four stereocenters, based on a new cerium(IV) ammonium nitrate catalyzed sequential three-component reaction.
The cerium(IV) ammonium nitrate (CAN)-catalyzed sequential, one-pot reaction between alkylamines, beta-ketoesters, and chalcones afforded cis-4,6-disubstituted 2-alkylaminocyclohexene-1-carboxylic esters with complete diastereoselectivity. The carbon-carbon double bond of these compounds was reduced with sodium triacetoxyborohydride, again with complete diastereoselectivity. This novel two-step route allows the transformation of very simple acyclic starting materials into tetrasubstituted cyclohexane derivatives bearing four functional groups, including a cis-beta-aminoester moiety, and generates four stereocenters, three of which are adjacent and one of which is quaternary.
Sridharan
Vellaisamy
V
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.
Menéndez
J Carlos
JC
D002384:Catalysis; D002563:Cerium / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D009566:Nitrates / Q000737:chemistry*; D013237:Stereoisomerism
D004952:Esters; D009566:Nitrates; C532772:cerium(IV) ammonium nitrate; D002563:Cerium