A Novel Stereoselective Route to (S)-(+)-α-(Fluoromethyl)histidine: α-Halomethylation of (2R,4S)-3-Benzoyl-2-(1,1-dimethylethyl)-1-methyl-4--1,3-imidazolidin-5-one. Synthesis and 1H NMR Spectroscopy

DOI: 10.1021/jo00055a027

Source and publish data:

Journal of Organic Chemistry p. 709 - 713 (1993)

Update date:2022-08-05

Topics: Synthesis Stereoselective 1H NMR spectroscopy

Authors:

Grozinger, Karl G.

Kriwacki, Richard W.

Leonard, Scott F.

Pitner, T. Phil

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Article abstract of DOI:10.1021/jo00055a027

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

Full text of DOI:10.1021/jo00055a027

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