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

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 synthesis

Publication History

Received: 15 November 2021

Accepted after revision: 17 December 2021

Article published online:
03 March 2022

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