Synlett 2022; 33(08): 759-766
DOI: 10.1055/s-0037-1610794
letter

Synthesis of Cyclopropyl Pinacol Boronic Esters from Dibromo­cyclopropanes

Zeina Neouchy
a   Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 – S4, 9000 Ghent, Belgium
,
Jan Hullaert
a   Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 – S4, 9000 Ghent, Belgium
,
b   Janssen Pharmaceutica NV, Turnhoutseweg 30, 2340 Beerse, Belgium
,
Lieven Meerpoel
b   Janssen Pharmaceutica NV, Turnhoutseweg 30, 2340 Beerse, Belgium
,
Jan-Willem Thuring
b   Janssen Pharmaceutica NV, Turnhoutseweg 30, 2340 Beerse, Belgium
,
Guido Verniest
b   Janssen Pharmaceutica NV, Turnhoutseweg 30, 2340 Beerse, Belgium
,
a   Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 – S4, 9000 Ghent, Belgium
› Author Affiliations
The authors thank Pharmaron for their contribution.


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Abstract

The synthesis of cyclopropyl pinacol boronic esters from dibromocyclopropanes via Matteson–Pasto rearrangement is reported. The method is readily scalable and shows limited levels of stereoinduction, with a selectivity that is in part complementary to that observed in existing stereoselective borylcyclopropanation strategies. The method can be used to rapidly access borylcyclopropanes as interesting building blocks for diversely functionalized cyclopropanes.

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Publication History

Received: 15 January 2022

Accepted after revision: 20 March 2022

Article published online:
19 April 2022

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