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Bae, Han Yong
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Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon-carbon bond forming reaction

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Title
Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon-carbon bond forming reaction
Author
Bae, Han YongHoefler, DenisKaib, Philip S. J.Kasaplar, PinarDe, Chandra KantaDoehring, ArnoLee, SunggiKaupmees, KarlLeito, IvoList, Benjamin
Issue Date
201808
Publisher
NATURE PUBLISHING GROUP
Citation
NATURE CHEMISTRY, v.10, no.8, pp.888 - 894
Abstract
The chemical synthesis of organic molecules involves, at its very essence, the creation of carbon-carbon bonds. In this context, the aldol reaction is among the most important synthetic methods, and a wide variety of catalytic and stereoselective versions have been reported. However, aldolizations yielding tertiary aldols, which result from the reaction of an enolate with a ketone, are challenging and only a few catalytic asymmetric Mukaiyama aldol reactions with ketones as electrophiles have been described. These methods typically require relatively high catalyst loadings, deliver substandard enantioselectivity or need special reagents or additives. We now report extremely potent catalysts that readily enable the reaction of silyl ketene acetals with a diverse set of ketones to furnish the corresponding tertiary aldol products in excellent yields and enantioselectivities. Parts per million (ppm) levels of catalyst loadings can be routinely used and provide fast and quantitative product formation in high enantiopurity. In situ spectroscopic studies and acidity measurements suggest a silylium ion based, asymmetric counter-anion-directed Lewis acid catalysis mechanism.
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DOI
http://dx.doi.org/10.1038/s41557-018-0065-0
ISSN
1755-4330
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