A novel stereoselective route to (S)-(+)-.alpha.-(fluoromethyl)histidine: .alpha.-halomethylation of (2R,4S)-3-benzoyl-2-(1,1-dimethylethyl)-1-methyl-4-[(N-tritylimidazol-4-yl)methyl]-1,3-imidazolidin-5-one. Synthesis and proton NMR spectroscopy

Autor:	Richard W. Kriwacki, Karl G. Grozinger, T. Phil Pitner, Scott F. Leonard
Rok vydání:	1993
Předmět:	Stereochemistry Chemistry Organic Chemistry Diastereomer Absolute configuration Stereoselectivity Nuclear magnetic resonance spectroscopy Enantiomer Alkylation Histidine Cis–trans isomerism
Zdroj:	The Journal of Organic Chemistry. 58:709-713
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00055a027
Popis:	A method is described for the α-enantioretentive methylation of L-histidine (S) to give (S)-(+)-α-(fluoromethyl)histidine (8). The synthesis involves the conversion of N im -trityl-L-histidine methyl ester (1) to both the «trans»-(2S,4S)- and «cis»-(2R,4S)-2-(1,1-dimethylethyl)-1-methyl-1,3-imidazolidin-5-one analogs 4 and 5. The cis isomer was regioselectively alkylated with chlorofluoromethane to give a single diastereomer 6 with retention of the original absolute configuration of the histidine α-position (S)
Databáze:	OpenAIRE
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