Catalytic enantioselective Michael addition of deconjugated butyrolactams to maleimides |
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Authors: | Bidisha Ray Santanu Mukherjee |
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Institution: | Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India |
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Abstract: | The first catalytic enantioselective Michael addition of deconjugated butyrolactams to N-arylmaleimides is developed with the help of a bifunctional tertiary aminosquaramide catalyst. Unlike the widely explored and structurally related vinylogous nucleophile – deconjugated butenolides, deconjugated butyrolactams are found to be exclusively α-selective. The resulting highly substituted and densely functionalized products, bearing contiguous all-carbon quaternary and tertiary stereocenters, are formed in good yields with moderate diastereoselectivity and good to excellent enantioselectivity (up to 99:1 er). |
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Keywords: | Corresponding author Michael addition Butyrolactam Maleimide All-carbon quaternary stereocenter Bifunctional catalysis |
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