Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

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Abstract: The synthesis of molecules bearing two or more contiguous, quaternary stereocenters is challenging, owing to the difficulty in controlling stereochemistry whilst simultaneously constructing a sterically congested motif. Herein, we report the electrophile‐induced ring contractive 1,2‐metallate rearrangement of 6‐membered cyclic alkenyl boronate complexes for the synthesis of cyclopentyl boronic esters bearing two contiguous, fully substituted stereocenters with high levels of stereocontrol. Remarkably, simple variation of the reaction solvent enabled their diastereodivergent construction with facile access to complementary diastereomeric pairs. The utility of our methodology is demonstrated in the asymmetric total synthesis of (+)‐herbertene‐1,14‐diol.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters ; day:23 ; month:06 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (23.06.2022) (gesamt 1)

Creator: Fairchild, Molly E.
Noble, Adam
Aggarwal, Varinder K.

DOI: 10.1002/anie.202205816

URN: urn:nbn:de:101:1-2022062715253825838760

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

Last update: 15.08.2025, 7:24 AM CEST

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Fairchild, Molly E.
Noble, Adam
Aggarwal, Varinder K.

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