Synlett 2019; 30(14): 1679-1682
DOI: 10.1055/s-0039-1690109
cluster
© Georg Thieme Verlag Stuttgart · New York

Scalable Synthesis of a Chiral Selenium π-Acid Catalyst and Its Use in Enantioselective Iminolactonization of β,γ-Unsaturated Amides

Yuta Otsuka
a  Department of Chemistry, Graduate School of Science, Chiba University, 1-33, Yayoi, Inage, Chiba, 263-8522, Japan   Email: takuya.hash@chiba-u.jp
b  Chiba Iodine Resource Innovation Center, 1-33, Yayoi, Inage, Chiba, 263-8522, Japan
,
Yuto Shimazaki
c  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan   Email: maruoka@kuchem.kyoto-u.ac.jp
,
Hitoshi Nagaoka
c  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan   Email: maruoka@kuchem.kyoto-u.ac.jp
,
Keiji Maruoka
c  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan   Email: maruoka@kuchem.kyoto-u.ac.jp
d  School of Chemical Engineering and Light Industry, Guangdong University of Technology, Panyu District, Guangzhou, 510006, P. R. of China
,
a  Department of Chemistry, Graduate School of Science, Chiba University, 1-33, Yayoi, Inage, Chiba, 263-8522, Japan   Email: takuya.hash@chiba-u.jp
b  Chiba Iodine Resource Innovation Center, 1-33, Yayoi, Inage, Chiba, 263-8522, Japan
c  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan   Email: maruoka@kuchem.kyoto-u.ac.jp
› Author Affiliations
T.H. thanks the Japan Society for the Promotion of Science (KAKENHI Grant Numbers JP16H01021 and JP18H04256 in Precisely Designed Catalysts with Customized Scaffolding, and JP19H02710). K.M. thanks the Japan Society for the Promotion of Science (KAKENHI Grant Numbers JP26220803 and JP17H06450).
Further Information

Publication History

Received: 13 May 2019

Accepted after revision: 18 June 2019

Publication Date:
28 June 2019 (online)


Published as part of the Cluster Organosulfur and Organoselenium Compounds in Catalysis

Abstract

Chiral selenium π-acid catalysis has for a long time been lagging behind other areas of asymmetric catalysis due to a lack of highly enantioselective catalysts. In this regard, we recently developed the first chiral selenium π-acid catalyst which performs the oxidative cyclization of β,γ-unsaturated carboxylic acids with high enantioselectivities. We report herein our improved synthesis of this chiral selenium catalyst, which allows access to a large quantity of the catalyst as the diselenide. In addition, the catalyst is tested in the oxidative cyclization of N-methoxy β,γ-unsaturated amides to give iminolactones with high enantioselectivities.

Supporting Information

 
  • References and Notes

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