Asymmetric Synthesis of 1,3-Oxazolidines via Intramolecular Aza-Michael Addition by Bifunctional Organocatalysts

• Fukata Yukihiro

  Department of Material Chemistry, Graduate School of Engineering, Kyoto University

• Asano Keisuke

  Department of Material Chemistry, Graduate School of Engineering, Kyoto University

• Matsubara Seijiro

  Department of Material Chemistry, Graduate School of Engineering, Kyoto University

Abstract

A novel synthetic route to optically active 1,3-oxazolidines via formal [3 + 2] cycloaddition in the presence of cinchona-alkaloid-thiourea-based bifunctional organocatalysts is reported. This protocol gives easy access to a wide range of chiral 1,3-oxazolidines. In addition, the results show that bifunctional organocatalysts can effect the intramolecular aza-Michael addition, leading to the asymmetric synthesis of nitrogen-containing heterocycles.

Journal

• Chemistry Letters

  Chemistry Letters 42 (4), 355-357, 2013

  The Chemical Society of Japan

Keywords

• General Chemistry

Details

• CRID: 1390282679565317504
• NII Article ID: 10031162171
• NII Book ID: AA00603318
• DOI: 10.1246/cl.121245
• COI: 1:CAS:528:DC%2BC3sXmvFKlur0%3D
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/42/4/355/55635144/cl.121245.pdf
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed