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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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
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Language:English
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cited_by cdi_FETCH-LOGICAL-a345t-f6c71a8fc2f5287ec73deeec59261dc30a1fd1fa7fa17a480ccfcc90985aaefe3
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container_title Organic letters
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creator Raja, Arun
Hong, Bor-Cherng
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description 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.
doi_str_mv 10.1021/acs.orglett.6b00459
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title 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
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