Dynamic Kinetic Asymmetric Synthesis of Five Contiguous Stereogenic Centers by Sequential Organocatalytic Stetter and Michael−Aldol Reaction: Enantioselective Synthesis of Fully Substituted Cyclopentanols Bearing a Quaternary Stereocenter

A synthesis of fully substituted cyclopentanes bearing a quaternary carbon center and five contiguous stereogenic centers has been achieved by sequential organocatalyzed Stetter and Michael−Aldol reactions of heteroaromatic aldehydes, nitroalkenes, and α,β-unsaturated aldehydes via the [1 + 2 + 2] a...

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Bibliographic Details
Published in:Organic letters 2011-03, Vol.13 (6), p.1338-1341
Main Authors: Hong, Bor-Cherng, Dange, Nitin S, Hsu, Che-Sheng, Liao, Ju-Hsiou, Lee, Gene-Hsiang
Format: Article
Language:English
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Summary:A synthesis of fully substituted cyclopentanes bearing a quaternary carbon center and five contiguous stereogenic centers has been achieved by sequential organocatalyzed Stetter and Michael−Aldol reactions of heteroaromatic aldehydes, nitroalkenes, and α,β-unsaturated aldehydes via the [1 + 2 + 2] annulation strategy with dynamic kinetic asymmetric transformation and excellent enantioselectivities (up to >99% ee).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200006e