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Synthesis 2022; 54(17): 3817-3822
DOI: 10.1055/s-0040-1719890
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
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.
Key words
allylboration - ring-closing metathesis - tandem catalysis - heterocycles - alcohols - stereoselective synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719890.
- Supporting Information
Publication History
Received: 15 November 2021
Accepted after revision: 17 December 2021
Article published online:
03 March 2022
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