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Acid-Induced and Reductive Transfor­mations of Enantiopure 3,6-Dihydro-2H-1,2-oxazines – Synthesis of Dideoxyamino Carbohydrate Derivatives

✍ Scribed by Bettina Bressel; Boris Egart; Ahmed Al-Harrasi; Robert Pulz; Hans-Ulrich Reißig; Irene Brüdgam

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
314 KB
Volume
2008
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Acid‐catalyzed transformations of carbohydrate‐derived 3,6‐dihydro‐2__H__‐1,2‐oxazines such as 1, 5 and 13 provided a set of enantiopure furano‐1,2‐oxazines or pyrano‐1,2‐oxazines. The reaction conditions determined the degree of solvolysis of the compounds. An X‐ray analysis of product 6 revealed an interesting network of hydrogen bonds. Reductive cleavage of the N–O bond of the 1,2‐oxazines either by hydrogen/palladium or by samarium diiodide furnished enantiopure aminofuran and ‐pyran derivatives, e.g. 9 and 11 or compound 16, which can be regarded as protected 4‐amino‐1,4‐dideoxyhex‐3‐ulose or 4‐amino‐1,4‐dideoxyoct‐3‐ulose derivatives. We thus have established a short and stereocontrolled route to amino carbohydrate derivatives with 1,2‐oxazines as crucial relay compounds. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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