Synthesis 2004(1): 20-22  
DOI: 10.1055/s-2003-42484
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of 2-Alkoxy-5-tert-butylmandelic Acid

Tomasz Bauer*, Joanna Gajewiak
Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland
Fax: +48(22)8225996; e-Mail: tbauer@chem.uw.edu.pl;
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Publikationsverlauf

Received 29 September 2003
Publikationsdatum:
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.

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The crystal structure has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 215036.