Organocatalytic enantioselective domino Michael-aldol condensation of 5-oxoalkanal and alpha,beta-unsaturated aldehydes. Efficient assembly of densely functionalized cyclohexenes.
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.
Hong
Bor-Cherng
BC
Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, Taiwan, ROC. chebch@ccu.edu.tw
Nimje
Roshan Y
RY
Sadani
Amit A
AA
Liao
Ju-Hsiou
JH