Stereodivergent Olefination of Enantioenriched Boronic Esters

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Abstract: 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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Stereodivergent Olefination of Enantioenriched Boronic Esters ; volume:129 ; number:3 ; year:2017 ; pages:804-808 ; extent:5
Angewandte Chemie ; 129, Heft 3 (2017), 804-808 (gesamt 5)

Creator: Armstrong, Roly J.
García‐Ruiz, Cristina
Myers, Eddie L.
Aggarwal, Varinder K.

DOI: 10.1002/ange.201610387

URN: urn:nbn:de:101:1-2022091807522551473423

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

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Associated

Armstrong, Roly J.
García‐Ruiz, Cristina
Myers, Eddie L.
Aggarwal, Varinder K.

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Synthesis of Boronic Ester γ‐Lactam Building Blocks

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