Inter- and intramolecular addition reactions of electron-deficient alkenes with alkyl radicals, generated by SET-photochemical decarboxylation of carboxylic acids, serve as a mild and efficient method for the preparation of gamma-amino acids and macrocyclic lactones

Yasuharu Yoshimi; Miho Masuda; Tomoyuki Mizunashi; Keisuke Nishikawa; Kousuke Maeda; Nobumasa Koshida; Tatsuya Itou; Toshio Morita; Minoru Hatanaka

doi:10.1021/ol9019277

Inter- and intramolecular addition reactions of electron-deficient alkenes with alkyl radicals, generated by SET-photochemical decarboxylation of carboxylic acids, serve as a mild and efficient method for the preparation of gamma-amino acids and macrocyclic lactones

Org Lett. 2009 Oct 15;11(20):4652-5. doi: 10.1021/ol9019277.

Authors

Yasuharu Yoshimi¹, Miho Masuda, Tomoyuki Mizunashi, Keisuke Nishikawa, Kousuke Maeda, Nobumasa Koshida, Tatsuya Itou, Toshio Morita, Minoru Hatanaka

Affiliation

¹ Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, 3-9-1 Bunkyo, Fukui 910-8507, Japan. yyoshimi@u-fukui.ac.jp

PMID: 19751053
DOI: 10.1021/ol9019277

Abstract

Inter- and intramolecular additions of alkyl radicals, generated by SET photochemical decarboxylation reactions of free carboxylic acids, to electron-deficient alkenes take place under mild conditions as part of efficient routes for the formation of N-Boc gamma-amino acids and macrocyclic lactones.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkanes / chemistry*
Alkenes / chemistry*
Amino Acids / chemistry*
Carboxylic Acids / chemistry*
Electron Transport
Electrons*
Lactones / chemistry*
Macrocyclic Compounds / chemistry
Photochemical Processes*

Substances

Alkanes
Alkenes
Amino Acids
Carboxylic Acids
Lactones
Macrocyclic Compounds