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A Facile Synthesis of Chiral Isocyanate-phenol and Unsymmetrical Urea Derived from Tyrosines without Protecting Phenolic Hydroxyl Groups

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A facile method for synthesis and isolation of chiral isocyanate-phenols, obtained from the reactions of L-tyrosine and L-DOPA [L-3-(3,4-dihydroxyphenyl)alanine] derivatives with di-tert-butyltricarbonate (DBTC), is described. Reaction of the obtained isocyanate-phenol with n-butylamine gave the corresponding chiral unsymmetrical urea.

Keywords: di-tert-butyltricarbonate; dopa; isocyanate; phenol; tyrosine; unsymmetrical; urea

Document Type: Review Article


Affiliations: Department of Polymer Science and Engineering, Faculty of Engineering, Yamagata University 4- 3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan;

Publication date: August 1, 2005

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.

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