Synthesis
DOI: 10.1055/s-0040-1719890
special topic
Special Issue in memory of Prof. Ferenc Fülöp

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

Francisco Garnes-Portolés
a   Departamento de Química Orgánica, Universidad de Valencia, Av. Vicent Andrés Estellés, 46100 Burjassot, Valencia, Spain
,
Rubén Miguélez
b   Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julian Clavería 8, 33006 Oviedo, Spain
,
Matthew N. Grayson
c   Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK
,
Pablo Barrio
a   Departamento de Química Orgánica, Universidad de Valencia, Av. Vicent Andrés Estellés, 46100 Burjassot, Valencia, Spain
b   Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julian Clavería 8, 33006 Oviedo, Spain
› Author Affiliations
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.


Dedicated to Professor Fülöp, in memoriam

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.

Supporting Information



Publication History

Received: 15 November 2021

Accepted after revision: 17 December 2021

Publication Date:
03 March 2022 (online)

© 2022. Thieme. All rights reserved

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