Organocatalytic enantioselective domino Michael-aldol condensation of 5-oxoalkanal and alpha,beta-unsaturated aldehydes. Efficient assembly of densely functionalized cyclohexenes |
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| Authors: | Hong Bor-Cherng Nimje Roshan Y Sadani Amit A Liao Ju-Hsiou |
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| Affiliation: | Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, Taiwan, ROC. chebch@ccu.edu.tw |
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| Abstract: | Organocatalytic Michael reaction of glutaraldehyde and 3-arylpropenal followed by the subsequent intramolecular aldol condensation provided 2-arylcyclohex-3-ene-1,3-dicarbaldehydes. Reactions with the 5-oxohexanal variant afforded the highly functionalized cyclohexenedicarbaldehydes in high diastereoselectivity and high enantioselectivity (>99% ee). Structure of the adduct 3j was confirmed unambiguously by X-ray analysis. |
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