Heteroatom-Tethered ω-Alkenylallylboronates: Stereoselective Synthesis of Heterocyclic Derived Alcohols

Francisco Garnes-Portolés, Rubén Miguélez, Matthew N. Grayson, Pablo Barrio

Research output: Contribution to journalArticlepeer-review

Abstract

The synthesis of ω-alkenylallylboronates using a heteroatom tether to join both functional groups is described for the first time. Then, these unprecedented compounds were used in a tandem Brønsted acid catalyzed allylboration/ring-closing metathesis (RCM) reaction affording heterocyclic derived alcohols as single diastereoisomers. The low enantioselectivity observed in the asymmetric version using a chiral phosphoric acid catalyst was studied theoretically.
Original languageEnglish
Pages (from-to)3817-3822
Number of pages6
JournalSynthesis
Volume54
Issue number17
Early online date3 Mar 2022
DOIs
Publication statusPublished - 31 Jul 2022

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