Organocatalytic Enantioselective Michael–Michael–Henry Reaction Cascade. An Entry to Highly Functionalized Hajos–Parrish-Type Ketones with Five to Six Contiguous Stereogenic Centers and Two Quaternary Carbons

An organocatalytic enantioselective reaction of 2-methylcyclopentane-1,3-dione, nitroalkene, and α,β-unsaturated aldehyde with the diphenylprolinol catalyst was developed to give the highly functionalized Hajos–Parrish-type ketones with five to six contiguous stereocenters and two quaternary carbon...

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Bibliographic Details
Published in:Organic letters 2016-04, Vol.18 (8), p.1760-1763
Main Authors: Raja, Arun, Hong, Bor-Cherng, Liao, Ju-Hsiou, Lee, Gene-Hsiang
Format: Article
Language:English
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Summary:An organocatalytic enantioselective reaction of 2-methylcyclopentane-1,3-dione, nitroalkene, and α,β-unsaturated aldehyde with the diphenylprolinol catalyst was developed to give the highly functionalized Hajos–Parrish-type ketones with five to six contiguous stereocenters and two quaternary carbon stereogenic centers with high diastereoselectivity and enantioselectivity. The structures of the adducts were unambiguously confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00459