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Enantioselective Catalysts for the Synthesis of α‐Substituted Allylboronates—An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols |
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| Authors: | M. Sc. Marcus Brauns Frédéric Muller Daniel Gülden Dr. Dietrich Böse Dr. Wolfgang Frey Dr. Martin Breugst Prof. Dr. Jörg Pietruszka |
| Affiliation: | 1. Institut für Bioorganische Chemie der, Heinrich-Heine-Universit?t Düsseldorf im, Forschungszentrum Jülich, Jülich, Germany;2. Department für Chemie, Universit?t zu K?ln, K?ln, Germany;3. Institut für Bio- und Geowissenschaften (IBG-1: Biotechnologie), Forschungszentrum Jülich, Jülich, Germany;4. Institut für Organische Chemie, Universit?t Stuttgart, Stuttgart, Germany;5. http://physorg.uni‐koeln.de;6. http://www.iboc.uni‐duesseldorf.de |
| Abstract: | The use of a convenient protecting group for boronates allows a selective, catalyzed SN2′ reaction to generate allylboronates which are applied for the synthesis of enantiomerically 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. |
| Keywords: | allylation asymmetric catalysis asymmetric synthesis boron computational chemistry |