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

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

doi:10.1055/s-0040-1719890

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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	3817-3822
Number of pages	6
Journal	Synthesis
Volume	54
Issue number	17
Early online date	3 Mar 2022
DOIs	https://doi.org/10.1055/s-0040-1719890
Publication status	Published - 31 Jul 2022

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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 Br{\o}nsted 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.",

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AU - Garnes-Portolés, Francisco

AU - Miguélez, Rubén

AU - Grayson, Matthew N.

AU - Barrio, Pablo

PY - 2022/7/31

Y1 - 2022/7/31

N2 - 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.

AB - 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.

U2 - 10.1055/s-0040-1719890

DO - 10.1055/s-0040-1719890

M3 - Article

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SP - 3817

EP - 3822

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 17

ER -

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

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