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ChemInform Abstract: Influence of a 2-Fluoro Substituent on Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Nitrones.

✍ Scribed by M. IHARA; Y. TANAKA; N. TAKAHASHI; Y. TOKUNAGA; K. FUKUMOTO

Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Influence of a 2-Fluoro Substituent on Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Nitrones.

-2-Fluoro nitrones, e.g. (IIIa)-(IIIc), show reverse diastereoselectivity in the title reaction compared with 2-hydro nitrones such as (IIId)-(IIIf). It is noteworthy that no appropriate catalyst for the reaction is found. Running the reaction under 10000 atm no improved yield and diastereoselectivity is observed. The syntheses of all starting materials are described and the stereochemistry of the products (V) and (VII) is determined after cyclization with TosOH to bicyclic systems. -(IHARA,

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