A Convenient Method for the Synthesis of Stable α-Fluoro Enamines of Nucleobases

Treatment of a whole set of nucleic acid bases and related derivatives 4, 9 and 10 with electron‐deficient hexafluoropropene or 1,1,3,3,3‐pentafluoropropene in the presence of sodium hydride gave the corresponding N1 and N9 stable fluorinated enamines with high regioselectivity. This alkylation is a...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2008-01, Vol.2008 (2), p.368-376
Main Authors: Wójtowicz-Rajchel, Hanna, Koroniak, Henryk, Katrusiak, Andrzej
Format: Article
Language:English
Subjects:
Addition-elimination reactions
Enamines
Hexafluoropropene
Nucleobases
Pentafluoropropene
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Summary:Treatment of a whole set of nucleic acid bases and related derivatives 4, 9 and 10 with electron‐deficient hexafluoropropene or 1,1,3,3,3‐pentafluoropropene in the presence of sodium hydride gave the corresponding N1 and N9 stable fluorinated enamines with high regioselectivity. This alkylation is a result of a Michael type addition–elimination process and gave the desired products 2a–10a and 2b–10b as E/Z mixtures. Unexpectedly, treatment of 2b with tert‐butyllithium and subsequently with [D4]methanol gave different results for E and Z stereoisomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700703