Chemo- and Regioselective Rhodium(I)-Catalyzed [2+2+2] Cycloaddition of Allenynes with Alkynes

Shigeo Yasuda; Yasuaki Kawaguchi; Yuta Okamoto; Chisato Mukai

doi:10.1002/chem.201602239

Chemo- and Regioselective Rhodium(I)-Catalyzed [2+2+2] Cycloaddition of Allenynes with Alkynes

Chemistry. 2016 Aug 16;22(34):12181-8. doi: 10.1002/chem.201602239. Epub 2016 Jul 20.

Authors

Shigeo Yasuda¹, Yasuaki Kawaguchi¹, Yuta Okamoto¹, Chisato Mukai²

Affiliations

¹ Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
² Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan. mukai@p.kanazawa-u.ac.jp.

PMID: 27436356
DOI: 10.1002/chem.201602239

Abstract

A highly chemo- and regioselective partially intramolecular rhodium(I)-catalyzed [2+2+2] cycloaddition of allenynes with alkynes is described. A range of diverse polysubstituted benzene derivatives could be synthesized in good to excellent yields, in which the allenynes served as synthetic equivalent to the diynes. A high regioselectivity could be observed when allenynes were treated with unsymmetrical alkynes.

Keywords: alkynes; allenes; cycloaddition; regioselectivity; rhodium.