Journal
SYNTHESIS-STUTTGART
Volume -, Issue 12, Pages 1887-1895Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1260469
Keywords
Michael addition; aldehydes; organocatalysis; aldol reaction; quinolines
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Funding
- National Science Council, Taiwan, ROC
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Organocatalytic domino double Michael reactions of ethyl (E)-7-oxohept-2-enoate and alpha,beta-unsaturated aldehydes provided ethyl 2-(2,4-diformyl-3-phenylcyclohexyl)acetate with excellent diastereoselectivities (>20:1 dr) and enantioselectivities (>99% ee). The adducts were further transformed to octahydro-3H-2-benzopyran-3-ones, octahydroisoquinolin-3(2H)-ones, and decahydro-5H-oxazolo[2,3-a]isoquinolin-5-ones.
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