Photoinduced electron transfer promoted radical ring expansion and cyclization reactions of α-(ω-carboxyalkyl) β-keto esters

Keisuke Nishikawa; Tomoki Ando; Kousuke Maeda; Toshio Morita; Yasuharu Yoshimi

doi:10.1021/ol303460u

Photoinduced electron transfer promoted radical ring expansion and cyclization reactions of α-(ω-carboxyalkyl) β-keto esters

Org Lett. 2013 Feb 1;15(3):636-8. doi: 10.1021/ol303460u. Epub 2013 Jan 23.

Authors

Keisuke Nishikawa¹, Tomoki Ando, Kousuke Maeda, Toshio Morita, Yasuharu Yoshimi

Affiliation

¹ Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, 3-9-1 Bunkyo, Fukui 910-8507, Japan.

PMID: 23343206
DOI: 10.1021/ol303460u

Abstract

Photoinduced electron transfer (PET) promoted decarboxylation of α-(ω-carboxyalkyl) β-keto esters undergoes radical ring expansion and cyclization reactions. This mild and environmentally friendly method can provide one-carbon expanded γ-keto esters and bicyclic alcohols, and the product distribution is strongly dependent on the length of the alkyl chain containing the terminal carboxylate group.