Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 50, Pages 12136-12140Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201701740
Keywords
allylation; asymmetric catalysis; boron; computational chemistry; quaternary stereogenic center
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Funding
- Deutsche Forschungsgemeinschaft DFG
- Fonds der Chemischen Industrie
- Heinrich-Heine-Universitat Dusseldorf
- Forschungszentrum Julich GmbH
- University of Cologne within the excellence initiative
- DFG
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An optimized protecting group for allylboronates allowed the use of ketones in order to synthesize all isomers of quaternary homoallylic alcohols with high enantioselectivities. All symmetric isomers of the allylboronate were prepared in high yields and diastereoselectivities using S(N)2' reactions. The improved reactivity of the novel protecting group was verified by following the reaction kinetics with H-1 NMR spectroscopy. Mechanistic studies using DFT calculations were conducted to investigate the new findings. Thus, the stereochemical outcome and enhanced reactivity can be rationalized.
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