Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 33, Pages 9610-9614Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201603894
Keywords
alpha-ketoesters; enantioselective synthesis; homoallylic alcohols; homogeneous catalysis; ketones
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Funding
- NIH [GM-57212]
- Olle Engkvist Byggmastare scholarship
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A set of broadly applicable methods for efficient catalytic additions of easy-to-handle allyl-B(pin) (pin=pinacolato) compounds to ketones and acyclic alpha-ketoesters was developed. Accordingly, a large array of tertiary alcohols can be obtained in 60 to > 98% yield and up to 99:1 enantiomeric ratio. At the heart of this development is rational alteration of the structures of the small-molecule aminophenol-based catalysts. Notably, with ketones, increasing the size of a catalyst moiety (tBu to SiPh3) results in much higher enantioselectivity. With alpha-ketoesters, on the other hand, not only does the opposite hold true, since Me substitution leads to substantially higher enantioselectivity, but the sense of the selectivity is reversed as well.
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