Enantioselective Pd-catalyzed allylic alkylation of indoles by a new class of chiral ferrocenyl P/S ligands

Hong Yee Cheung; Wing-Yiu Yu; Fuk Loi Lam; Terry T-L Au-Yeung; Zhongyuan Zhou; Tak Hang Chan; Albert S C Chan

doi:10.1021/ol7018532

Enantioselective Pd-catalyzed allylic alkylation of indoles by a new class of chiral ferrocenyl P/S ligands

Org Lett. 2007 Oct 11;9(21):4295-8. doi: 10.1021/ol7018532. Epub 2007 Sep 13.

Authors

Hong Yee Cheung¹, Wing-Yiu Yu, Fuk Loi Lam, Terry T-L Au-Yeung, Zhongyuan Zhou, Tak Hang Chan, Albert S C Chan

Affiliation

¹ Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.

PMID: 17850156
DOI: 10.1021/ol7018532

Abstract

Chiral ferrocenyl heterobidentate P/S ligands bearing both central and planar chirality were prepared from (S)-Ugi's amine via a three-step modular synthesis. Through systematic screening and optimization, L8 was found to be the best ligand for Pd-catalyzed asymmetric allylic alkylation of indoles with ee's up to 96% being attained.