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A Convenient Method for the Synthesis of Stable α‐Fluoro Enamines of Nucleobases
Author(s) -
WójtowiczRajchel Hanna,
Koroniak Henryk,
Katrusiak Andrzej
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700703
Subject(s) - chemistry , regioselectivity , sodium hydride , nucleobase , alkylation , nucleic acid , methanol , hydride , butyllithium , medicinal chemistry , organic chemistry , stereochemistry , dna , hydrogen , catalysis , biochemistry
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 N 1 and N 9 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 [D 4 ]methanol gave different results for E and Z stereoisomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)