Diastereoselective synthesis of 2-alkoxy-5-tert-butylmandelic acid

Lewis acid catalyzed addition of N-glyoxyloyl-(2R)-bornane-10,2-sultam to O-protected 4-tert-butylphenols is presented. The reactions proceed with excellent diastereoselectivities. The products of the addition are hydrolyzed with LiOH.H2O yielding optically pure alpha-hydroxycarboxylic acids.

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 1; pp. 20 - 22
Main Authors Bauer, T, Gajewiak, J
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 05.01.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Friedel-Crafts reactions
phenols
diastereoselectivity
glyoxylate
Oppolzer's sultam
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Summary:Lewis acid catalyzed addition of N-glyoxyloyl-(2R)-bornane-10,2-sultam to O-protected 4-tert-butylphenols is presented. The reactions proceed with excellent diastereoselectivities. The products of the addition are hydrolyzed with LiOH.H2O yielding optically pure alpha-hydroxycarboxylic acids.
ISSN:0039-7881
DOI:10.1055/s-2003-42484