Highly regio- and stereoselective synthesis of alkylidenecyclopropanes via Ru(II)-Pheox catalyzed asymmetric inter- and intramolecular cyclopropanation of allenes

Soda Chanthamath; Hao Wei Chua; Seiya Kimura; Kazutaka Shibatomi; Seiji Iwasa

doi:10.1021/ol5014944

Highly regio- and stereoselective synthesis of alkylidenecyclopropanes via Ru(II)-Pheox catalyzed asymmetric inter- and intramolecular cyclopropanation of allenes

Org Lett. 2014 Jun 20;16(12):3408-11. doi: 10.1021/ol5014944. Epub 2014 Jun 11.

Authors

Soda Chanthamath¹, Hao Wei Chua, Seiya Kimura, Kazutaka Shibatomi, Seiji Iwasa

Affiliation

¹ Department of Environmental, Life Sciences, Toyohashi University of Technology , 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.

PMID: 24918864
DOI: 10.1021/ol5014944

Abstract

An efficient protocol for the synthesis of optically active alkylidenecyclopropanes (ACPs) via the Ru(II)-Pheox catalyzed asymmetric cyclopropanation of allenes has been established. This catalytic system proceeded with high regioselectivity to give the ACP products in high yield with high diastereoselectivity (up to 99/1) and enantioselectivity (up to 99% ee).