5- exo-Selective asymmetric bromolactonization of stilbenecarboxylic acids catalyzed by phenol-bearing chiral thiourea

Masayuki Sugano; Tsubasa Inokuma; Yousuke Yamaoka; Ken-Ichi Yamada

doi:10.1039/d3ob01895d

5- exo-Selective asymmetric bromolactonization of stilbenecarboxylic acids catalyzed by phenol-bearing chiral thiourea

Org Biomol Chem. 2024 Feb 28;22(9):1765-1769. doi: 10.1039/d3ob01895d.

Authors

Masayuki Sugano¹, Tsubasa Inokuma^{1

2}, Yousuke Yamaoka³, Ken-Ichi Yamada^{1

2}

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan. yamak@tokushima-u.ac.jp.
² Research Cluster on "Key Material Development, " Tokushima University, Shomachi, Tokushima 770-8505, Japan.
³ Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 38099597
DOI: 10.1039/d3ob01895d

Abstract

We developed a novel thiourea Lewis-base catalyst with phenol moieties for the enantioselective 5-exo-bromolactonization of stilbenecarboxylic acids to afford chiral 3-substituted phthalides. The phenol moieties are crucial for the enantio- and regio-selectivity.