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Strain Release of Donor–Acceptor Cyclopropyl Boronate Complexes

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)3412-3416
Number of pages5
JournalOrganic Letters
Volume21
Issue number9
Early online date24 Apr 2019
DOIs
DateAccepted/In press - 24 Apr 2019
DateE-pub ahead of print - 24 Apr 2019
DatePublished (current) - 3 May 2019

Abstract

The reactivity of boronate complexes which resemble donor–acceptor cyclopropanes is described. The enantioenriched cyclopropyl boronate complexes were shown to undergo concerted 1,2-metalate rearrangement/ring opening upon activation with a Lewis acid. This method provides atom-efficient access to optically active γ-carbonyl boronic esters in moderate to excellent yields with complete enantiospecificity. Furthermore, a three-component variant of the reaction was established through in situ alkylation, and the synthetic utility of the products as chiral building blocks was demonstrated.

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    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at https://pubs.acs.org/doi/10.1021/acs.orglett.9b01152 . Please refer to any applicable terms of use of the publisher.

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