A highly tunable stereoselective dimerization of methyl ketone: efficient synthesis of E- and Z-1,4-enediones

Kun Xu; Yang Fang; Zicong Yan; Zhenggen Zha; Zhiyong Wang

doi:10.1021/ol4006344

A highly tunable stereoselective dimerization of methyl ketone: efficient synthesis of E- and Z-1,4-enediones

Org Lett. 2013 May 3;15(9):2148-51. doi: 10.1021/ol4006344. Epub 2013 Apr 16.

Authors

Kun Xu¹, Yang Fang, Zicong Yan, Zhenggen Zha, Zhiyong Wang

Affiliation

¹ CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, PR China.

PMID: 23590409
DOI: 10.1021/ol4006344

Abstract

A new method for the tunable synthesis of 1,4-enedione directly from aromatic methyl ketone is described. This tandem reaction enables the construction of symmetric and unsymmetric 1,4-enediones with complete E-selectivity. Moreover, the resulting E-1,4-enedione could be transformed into a Z-isomer by irradiation with 23 W of white light.