Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 4, Pages 1548-1552Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201509198
Keywords
allylation; asymmetric catalysis; asymmetric synthesis; boron; computational chemistry
Categories
Funding
- Deutsche Forschungsgemeinschaft DFG
- Fonds der Chemischen Industrie
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The use of a convenient protecting group for boronates allows a selective, catalyzed S(N)2' reaction to generate allylboronates which are applied for the synthesis of enantio-merically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four possible stereoisomers can be formed. The rationale behind the selective addition is supported by density functional theory calculations.
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