Chiral bifunctional sulfide-catalyzed enantioselective bromolactonizations of α- and β-substituted 5-hexenoic acids

Sao Sumida; Ken Okuno; Taiki Mori; Yasuaki Furuya; Seiji Shirakawa

doi:10.3762/bjoc.20.158

Chiral bifunctional sulfide-catalyzed enantioselective bromolactonizations of α- and β-substituted 5-hexenoic acids

Beilstein J Org Chem. 2024 Jul 30:20:1794-1799. doi: 10.3762/bjoc.20.158. eCollection 2024.

Authors

Sao Sumida¹, Ken Okuno¹, Taiki Mori¹, Yasuaki Furuya¹, Seiji Shirakawa¹

Affiliation

¹ Institute of Integrated Science and Technology, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.

Abstract

Enantioselective halolactonizations of sterically less hindered alkenoic acid substrates without substituents on the carbon-carbon double bond have remained a formidable challenge. To address this limitation, we report herein the asymmetric bromolactonization of 5-hexenoic acid derivatives catalyzed by a BINOL-derived chiral bifunctional sulfide.

Keywords: asymmetric catalysis; enantioselectivity; halogenation; lactones; organocatalysis.

Grants and funding

K.O. thanks the JSPS for a research fellowship (DC2). T.M. thanks the Nagasaki University for a planetary health research fellowship. This work was supported by JSPS KAKENHI (Grant Numbers 23K04752 for S. Shirakawa & 24KJ1826 for K.O.), and the Joint Usage/Research Center for Catalysis (24DS0655 for S. Shirakawa).