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Microwave assisted synthesis of enantiomerically pure allylboronates |
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| Authors: | Vesna Cmrecki Wolfgang Frey |
| Institution: | a Institut für Bioorganische Chemie, Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, Stetternicher Forst Geb. 15.8, 52428 Jülich, Germany b Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany |
| Abstract: | Stable allylboronates with a stereogenic centre α to the boronic ester moiety represent versatile reagents for stereoselective synthesis of homoallylic alcohols. Use of microwave irradiation in desilylation and sigmatropic rearrangement reactions allows rapid synthesis of α-chiral allylboronates utilized in the highly diastereo- and enantioselective synthesis of (Z)-configured homoallylic α-hydroxy esters by allyl additions to ethyl glyoxylate. |
| Keywords: | Asymmetric synthesis Sigmatropic rearrangement Microwave chemistry Allyl addition Boronic esters |
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