Volume 27, Issue 23
Natural Products
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ChemInform Abstract: Synthesis of Nitrogen-Containing Unsaturated Carbohydrates via an Allyl Cyanate-to-Isocyanate Rearrangement.

Y. ICHIKAWA

Y. ICHIKAWA

Lab. Org. Chem., Sch. Agric. Sci., Nagoya Univ., Chikusa, Nagoya 464- 01, Japan

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C. KOBAYASHI

C. KOBAYASHI

Lab. Org. Chem., Sch. Agric. Sci., Nagoya Univ., Chikusa, Nagoya 464- 01, Japan

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M. ISOBE

M. ISOBE

Lab. Org. Chem., Sch. Agric. Sci., Nagoya Univ., Chikusa, Nagoya 464- 01, Japan

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First published: June 4, 1996

Abstract

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ChemInform Abstract

A new method for the preparation of nitrogen-containing unsaturated carbohydrates, e.g. (VIII), (X), and (XV) is developed. The method involves dehydration of the allyl carbamates (VI) or (XIV) to give the corresponding allyl cyanates, which undergo (3,3) sigmatropic rearrangement into allylic isocyanates. Trapping with amines or Me3Al affords either the allyl urea (VIII) or the acetamides (X) and (XV).

chemical structure image

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