Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence.
A one-pot, asymmetric multicatalytic formal [3+2] reaction between 1,3-dicarbonyls and alpha,beta-unsaturated aldehydes is described. The multicatalytic process involves a secondary amine catalyzed Michael addition followed by a N-heterocyclic carbene catalyzed intramolecular crossed benzoin reaction to afford densely functionalized cyclopentanones with high enantioselectivities. The reaction proceeds with a variety of alkyl and aryl enals as well as a range of 1,3-dicarbonyls (diketones and beta-ketoesters). The functionalized products are obtained from cheap, readily available starting materials in a rapid and efficient manner in a one-pot, one-step operation.
Lathrop
Stephen P
SP
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Rovis
Tomislav
T
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D003517:Cyclopentanes; C007201:cyclopentanone; C030011:carbene; D008697:Methane