Synfacts 2018; 14(03): 0259
DOI: 10.1055/s-0037-1609264
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Cycloaddition of Cyclopropylcarboxamides to Alkynes

Hisashi Yamamoto
Takahiro Sawano
Liu Q.-S. Wang D.-Y. Yang Z.-J. Luan Y.-X. Yang J.-F. Li J.-F. Pu Y.-G. Ye M. * Nankai University, Tianjin, P. R. of China
Ni–Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne.

J. Am. Chem. Soc. 2017;
139: 18150-18153
Further Information

Publication History

Publication Date:
15 February 2018 (online)



Transition-metal-catalyzed cyclo­addition of cyclopropanes to π-unsaturated compounds is a useful method for the formation of ­cyclic compounds that has been studied over recent decades. However, the reaction with cyclopropylcarboxamides remains challenging due to their relatively low reactivity. The authors have developed a Ni–Al bimetallic system that facilitates the cycloaddition reaction of cyclopropylcarboxamides to alkynes.



Whereas a nonenantioselective reaction was achieved by using Ph2P(O)H as a bifunctional ligand, a TADDOL-derived chiral ligand realized highly enantioselective cycloaddition reactions.