Convenient syntheses of 2-, 5- and 6-fluoro- and 2,6-difluoro- l-DOPA

Convenient syntheses of 2-, 5- and 6-fluoro- and 2,6-difluoro- l-DOPA

Alkylation under phase transfer conditions of the chiral glycine synthon 2 (prepared from the commercially available Oppolzer chiral sultam) with fluorinated analogues of 3,4-dimethoxybenzyl chloride proceeded with high diastereoselectivity. Hydrolysis of the Schiff base, removal of the chiral auxil...

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Bibliographic Details
Published in:Tetrahedron: asymmetry Vol. 13; no. 11; pp. 1135 - 1140
Main Authors: Deng, Wei-Ping, Wong, Kelli A., Kirk, KennethL
Format: Journal Article
Language:English
Published: Elsevier Ltd 21-06-2002
Online Access:Get full text
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Summary:Alkylation under phase transfer conditions of the chiral glycine synthon 2 (prepared from the commercially available Oppolzer chiral sultam) with fluorinated analogues of 3,4-dimethoxybenzyl chloride proceeded with high diastereoselectivity. Hydrolysis of the Schiff base, removal of the chiral auxiliary and HBr demethylation produced 2-, 5-, 6-fluoro- and 2,6-difluoro- l-DOPA in e.e. of >99%. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(02)00321-X