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Synlett 2014; 25(07): 1026-1030
DOI: 10.1055/s-0033-1340859
letter
© Georg Thieme Verlag Stuttgart · New York

Facile Preparation of 1,5-Diazacyclooctanes from Unsaturated Imines: Effects of the Hydroxyl Groups on [4+4] Dimerization

Katsunori Tanaka*
a   Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan   Fax: +81(48)4679405   Email: kotzenori@riken.jp
,
Risa Matsumoto
b   Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
,
Ambara R. Pradipta
a   Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan   Fax: +81(48)4679405   Email: kotzenori@riken.jp
,
Yasutaka Kitagawa
b   Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
,
Mitsutaka Okumura
b   Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
,
Yoshiyuki Manabe
b   Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
,
Koichi Fukase
b   Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
› Author Affiliations
Further Information

Publication History

Received: 08 January 2014

Accepted after revision: 04 February 2014

Publication Date:
18 March 2014 (online)

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Abstract

Hydroxyl groups on an unsaturated imine, which may be readily obtained from the corresponding unsaturated aldehyde and the 1,2-ethanolamine derivative, were found to efficiently activate a [4+4] dimerization reaction to produce the eight-membered 1,5-diazacyclooctane. A novel OH–π interaction between the two imines, in addition to the stabilization of the eight-membered diacetals, was proposed based on density functional theory calculations.

Key words

1,5-diazacyclooctanes - unsaturated imines - hydroxyl groups - [4+4] dimerization

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • Reference

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