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

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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 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

Funding

P.B. thanks the Ministerio de Economía y Competitividad (MINECO, Spain) for a Ramón y Cajal contract (RyC-2016-20951). M.N.G. thanks the University of Bath for financial support.MiniseiodeEconomíayCompetividadRyC-2016-20951UnivesiytofBah

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© Thieme. The final publication is available at Synthesis: Journal of Synthetic Organic Chemistry via https://doi.org/10.1055/s-0040-1719890
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Cite this

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title = "Heteroatom-Tethered ω-Alkenylallylboronates: Stereoselective Synthesis of Heterocyclic Derived Alcohols",

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.",

author = "Francisco Garnes-Portol{\'e}s and Rub{\'e}n Migu{\'e}lez and Grayson, {Matthew N.} and Pablo Barrio",

year = "2022",

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doi = "10.1055/s-0040-1719890",

language = "English",

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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.

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DO - 10.1055/s-0040-1719890

M3 - Article

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VL - 54

SP - 3817

EP - 3822

JO - Synthesis

JF - Synthesis

IS - 17

ER -

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

Abstract

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Avance 300 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Raman confocal microscope RENISHAM INVIA

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