Download PDF
Synfacts 2015; 11(6): 0613-0615
DOI: 10.1055/s-0034-1380886
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Cyclization of Ene-Allenes by Nickel Catalysis

Contributor(s):
Mark Lautens
,
Charles C. J. Loh
Noucti NN, Alexanian EJ * The University of North Carolina at Chapel Hill, USA
Stereoselective Nickel-Catalyzed [2+2] Cycloadditions of Ene-Allenes.

Angew. Chem. Int. Ed. 2015;
54: 5447-5450
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
18 May 2015 (online)

 
 PDF Download Permissions and Reprints

Key words

nickel - ene-allenes - [2+2] cycloaddition

Significance

The [2+2] cycloaddition of ene-allenes is a powerful methodology in the construction of fused cyclobutanes. However, one of the challenges of known protocols is the limited substrate scope, tolerating only styrene or diene π-components. Alexanian and Noucti demonstrate the utility of nickel catalysis in a stereoselective [2+2]-cycloaddition to generate diverse carbocyclic frameworks A.


#

Comment

It is noteworthy to point out the effectiveness of this protocol to cyclize terminal allenes which are not tolerated in other known methods. Moreover, an interesting observation was discovered where methyl substitution at R2 changes the [2+2] cycloaddition from the proximal to the distal π-bond of the allene, generating the bicyclo[4.2.2] scaffold B instead.


#
#


   Permissions and Reprints