Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 3, Pages 786-790Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610387
Keywords
alkenes; boron; isomers; oxidation; selenium
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Funding
- Ramon Areces Foundation
- EPSRC [EP/I038071/1]
- Bristol University
- EPSRC [EP/K03927X/1, EP/I038071/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1, EP/I038071/1] Funding Source: researchfish
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A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.
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