Copper(I)-Catalyzed Enantioselective 1,6-Borylation of α,β,γ,δ-Unsaturated Phosphonates

Hyesu Lee; Jaesook Yun

doi:10.1021/acs.orglett.8b03532

Copper(I)-Catalyzed Enantioselective 1,6-Borylation of α,β,γ,δ-Unsaturated Phosphonates

Org Lett. 2018 Dec 21;20(24):7961-7964. doi: 10.1021/acs.orglett.8b03532. Epub 2018 Dec 3.

Authors

Hyesu Lee¹, Jaesook Yun¹

Affiliation

¹ Department of Chemistry and Institute of Basic Science , Sungkyunkwan University , Suwon 16419 , Korea.

PMID: 30507202
DOI: 10.1021/acs.orglett.8b03532

Abstract

Copper(I)-catalyzed asymmetric 1,6-borylation of 1,3-dienylphosphonates was achieved using ( S, S)-Ph-BPE as a chiral ligand. Regio-, stereo-, and enantioselective borylation successfully proceeded to afford phosphonate-containing allylboronates, with high enantioselectivity up to 97% ee. Further applications of the resulting products generated a valuable phosphonate analogue of γ-butyrolactone.

Publication types

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