Abstract
With the aid of an appropriate chiral catalyst, acyclic silyl ketene acetals react with anhydrides to furnish 1,3-dicarbonyl compounds that bear all-carbon quaternary stereocenters in good ee and yield. Mechanistic studies provide strong support for a catalytic cycle that involves activation of both the electrophile (anhydride --> acylpyridinium) and the nucleophile (silyl ketene acetal --> enolate).
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Acetals / chemistry*
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Acylation
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Anhydrides / chemistry
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Catalysis
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Ethylenes / chemistry*
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Ketones / chemistry*
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Pyridinium Compounds / chemistry
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Silanes / chemistry*
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Stereoisomerism
Substances
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Acetals
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Anhydrides
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Ethylenes
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Ketones
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Pyridinium Compounds
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Silanes
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ketene