Asymmetric Synthesis of Functionalized Cyclopentanones via a Multicatalytic Secondary Amine/ N -Heterocyclic Carbene Catalyzed Cascade Sequence
2009; American Chemical Society; Volume: 131; Issue: 38 Linguagem: Inglês
10.1021/ja905342e
ISSN1943-2984
AutoresStephen P. Lathrop, Tomislav Rovis,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoA one-pot, asymmetric multicatalytic formal [3+2] reaction between 1,3-dicarbonyls and α,β-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 β-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.
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