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

Katsunori Tanaka; Risa Matsumoto; Ambara R. Pradipta; Yasutaka Kitagawa; Mitsutaka Okumura; Yoshiyuki Manabe; Koichi Fukase

doi:10.1055/s-0033-1340859

Synlett, Table of Contents

Synlett 2014; 25(07): 1026-1030
DOI: 10.1055/s-0033-1340859

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

Authors

Katsunori Tanaka*

^aBiofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan Fax: +81(48)4679405 Email: kotzenori@riken.jp
Risa Matsumoto

^bDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
Ambara R. Pradipta

^aBiofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan Fax: +81(48)4679405 Email: kotzenori@riken.jp
Yasutaka Kitagawa

^bDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
Mitsutaka Okumura

^bDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
Yoshiyuki Manabe

^bDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
Koichi Fukase

^bDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan

Abstract

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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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References

Reference
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Supplementary Material

Supporting Information (PDF)