Asymmetric Cycloetherifications by Bifunctional Aminothiourea Catalysts: The Importance of Hydrogen Bonding

• Fukata, Yukihiro

• Miyaji, Ryota

• Okamura, Takaaki

• Asano, Keisuke

• Matsubara, Seijiro

Abstract

Chiral oxacyclic frameworks are prevalent in many natural products and bioactive compounds. In addition, a number of them are important synthetic intermediates. Thus, the synthesis of such structures is a significant goal in the field of organic chemistry. However, the development of catalytic asymmetric cycloetherification for the straightforward synthesis of these compounds remains a challenge. In this study, we propose the use of aminothiourea catalysis as an effective way to accomplish such a challenge. The asymmetric synthesis of chiral oxygen heterocycles, including tetrahydrofurans, tetrahydropyrans, and 1, 3-dioxolanes, is demonstrated herein using intramolecular oxy-Michael addition mediated by bifunctional aminothiourea catalysts.

Journal

• Synthesis

  Synthesis 45 (12), 1627-1634, 2013-06-05

  Thieme Publishing

Keywords

• oxycyclization
• cycloetherification
• hydrogen bonding
• bifunctional aminothiourea catalyst
• oxy-Michael addition

Details

• CRID: 1050845760726975360
• NII Article ID: 120005474484
• NII Book ID: AA00855740
• ISSN: 00397881
• ISSN: 1437210X
• DOI: 10.1055/s-0032-1316920
• HANDLE: 2433/189760
• Web Site: http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0032-1316920.pdf
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN