4.4 Article

A convenient synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-threo-(3,4-dihydroxyphenyl)serine using Sharpless asymmetric aminohydroxylation

Journal

TETRAHEDRON LETTERS
Volume 42, Issue 48, Pages 8401-8403

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)01816-0

Keywords

2-fluoro- and 6-fluoro-(2S,3R)-threo-(3,4-dihydroxyphenyl)serine; Sharpless asymmetric aminohydroxylation; regioselectivity; enantioselectivity

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Ring-fluorinated beta -hydroxy alpha -amino methyl esters 3b,c were synthesized enantio selectively using Sharpless asymmetric amino hydroxylation. These were converted to 2-fluoro- and 6-fluoro-(2S,3R)-threo-(3,4-dihydroxyphenyl)serine 1b,c using our previously published procedure. (C) 2001 Elsevier Science Ltd. All rights reserved.

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