Synthesis 2013; 45(12): 1627-1634
DOI: 10.1055/s-0032-1316920
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Yukihiro Fukata
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan   Fax: +81(75)3832438   Email: keisuke.asano@t03kr913mk.mbox.media.kyoto-u.ac.jp   Email: matsubara.seijiro.2e@kyoto-u.ac.jp
,
Ryota Miyaji
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan   Fax: +81(75)3832438   Email: keisuke.asano@t03kr913mk.mbox.media.kyoto-u.ac.jp   Email: matsubara.seijiro.2e@kyoto-u.ac.jp
,
Takaaki Okamura
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan   Fax: +81(75)3832438   Email: keisuke.asano@t03kr913mk.mbox.media.kyoto-u.ac.jp   Email: matsubara.seijiro.2e@kyoto-u.ac.jp
,
Keisuke Asano*
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan   Fax: +81(75)3832438   Email: keisuke.asano@t03kr913mk.mbox.media.kyoto-u.ac.jp   Email: matsubara.seijiro.2e@kyoto-u.ac.jp
,
Seijiro Matsubara*
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan   Fax: +81(75)3832438   Email: keisuke.asano@t03kr913mk.mbox.media.kyoto-u.ac.jp   Email: matsubara.seijiro.2e@kyoto-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 21 February 2013

Accepted after revision: 20 March 2013

Publication Date:
16 April 2013 (online)

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.

Supporting Information

 
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