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.
Sao Sumida  1 ,  Ken Okuno  1 ,  Taiki Mori  1 ,  Yasuaki Furuya  1 ,  Seiji Shirakawa  1
Affiliations
  • 1. Institute of Integrated Science and Technology, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
PMID: 39109297 DOI: 10.3762/bjoc.20.158
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.
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