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New Enantioselective Synthesis of Monofluorinated Pyridines Designed for the Preparation of Chemical Libraries

✍ Scribed by Anne-Laure Blayo; Stéphanie Le Meur; Danielle Grée; René Grée

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
193 KB
Volume
350
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

Chiral pyridines with a fluorine atom in the benzylic position are easily accessible from optically active propargylic fluorides by using the Bohlmann–Rahtz reaction. Such pyridines, possessing four points of molecular diversity, are useful scaffolds for the preparation of chemical libraries.

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m. p.=248-250GC (dec.; from methanol); [.ID= -129.' (DMSO, c = 1.00); 'H-NMR (D6-DMSO); t=4.13 and 4.18 (s, I-H+l'-H and s, 2 2-benzyl-H, or vice versa); MS: 520 (M+)]. The amino ketone ( 8 ) is probably first formed, being later aromatized by dimerization and air oxidation to yield ( 9 ) . The firs