Synfacts 2018; 14(11): 1175
DOI: 10.1055/s-0037-1611035
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Stereodefined Unsaturated Acyclic Fragments

Contributor(s):
Paul Knochel
,
Moritz Balkenhohl
Bruffaerts J, Pierrot D, Marek I. * Technion-Israel Institute of Technology, Haifa, Israel
Efficient and Stereodivergent Synthesis of Unsaturated Acyclic Fragments Bearing Contiguous Stereogenic Elements.

Nat. Chem. 2018;
DOI: DOI: 10.1038/s41557-018-0123-7.
Further Information

Publication History

Publication Date:
18 October 2018 (online)

 

Significance

Marek and co-workers report a highly stereodivergent route to unsaturated acyclic fragments in good to excellent yields. The key step for this transformation is the oxidative palladium-catalyzed Heck coupling of aryl boronic acids with alkenylcyclopropyl carbinols.


#

Comment

Remarkably, by using this method, all four stereoisomers of similar scaffolds can be synthesized. Furthermore, in addition to various arylboronic acids, alkenyl triflates or heteroarylboronic acids can be employed in the Heck reaction.


#
#