Sequential Organocatalytic Stetter and Michael-Aldol Condensation Reaction: Asymmetric Synthesis of Fully Substituted Cyclopentenes via a [1 + 2 + 2] Annulation Strategy

A stereoselective synthesis of fully substituted cyclopentenes has been achieved by a sequential organocatalyzed Stetter and Michael-aldol condensation of aromatic aldehydes, nitroalkenes, and α,β-unsaturated aldehydes via the [1 + 2 + 2] annulation strategy with excellent diastereoselectivities and...

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Veröffentlicht in:Organic letters 2010-11, Vol.12 (21), p.4812-4815
Hauptverfasser: Hong, Bor-Cherng, Dange, Nitin S, Hsu, Che-Sheng, Liao, Ju-Hsiou
Format: Artikel
Sprache:eng
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Zusammenfassung:A stereoselective synthesis of fully substituted cyclopentenes has been achieved by a sequential organocatalyzed Stetter and Michael-aldol condensation of aromatic aldehydes, nitroalkenes, and α,β-unsaturated aldehydes via the [1 + 2 + 2] annulation strategy with excellent diastereoselectivities and enantioselectivities (up to >99% ee).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101969t