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Synthesis 2009(14): 2329-2332  
DOI: 10.1055/s-0029-1216843
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Oxidative Conversion of Aldehydes into 2-Substituted 2-Oxazolines Using 1,3-Diiodo-5,5-dimethylhydantoin

Shogo Takahashi, Hideo Togo*
Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
Fax: +81(43)2902874; e-Mail: togo@faculty.chiba-u.jp;
Further Information

Publication History

Received 5 February 2009
Publication Date:
25 May 2009 (online)

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Abstract

Various aromatic and aliphatic aldehydes were converted into the corresponding 2-aryl and 2-alkyl-2-oxazolines, respectively, in good to high yields by reaction with 2-aminoethanol and 1,3-diiodo-5,5-dimethylhydantoin. Moreover, chiral bis-2-oxazolines, which can be used as chiral ligands in asymmetric synthesis, could be also prepared in moderate yields by the reaction of dialdehydes with (R)-(-)-2-phenylglycinol under the same conditions.

Key words

2-aryl-2-oxazoline - 2-alkyl-2-oxazoline - 1,3-diiodo-5,5-dimethylhydantoin - aldehyde - 2-aminoethanol - chiral oxazoline

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