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Synthesis 2004(1): 20-22
DOI: 10.1055/s-2003-42484
DOI: 10.1055/s-2003-42484
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Diastereoselective Synthesis of 2-Alkoxy-5-tert-butylmandelic Acid
Further Information
Publication History
Received
29 September 2003
Publication Date:
17 November 2003 (online)


Abstract
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 α-hydroxycarboxylic acids.
Key words
diastereoselectivity - Friedel-Crafts reactions - glyoxylate - Oppolzer’s sultam - phenols