Synthesis, Table of Contents SHORTPAPER © Georg Thieme Verlag Stuttgart · New York Diastereoselective Synthesis of 2-Alkoxy-5-tert-butylmandelic Acid Tomasz Bauer*, Joanna GajewiakDepartment of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, PolandFax: +48(22)8225996; e-Mail: tbauer@chem.uw.edu.pl; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References References 1 Bauer T. Tarasiuk J. Tetrahedron Lett. 2002, 43: 687 2a Bigi F. Sartori G. Maggi R. Cantarelli E. Galaverna G. Tetrahedron: Asymmetry 1993, 4: 2411 2b Bigi F. Bocelli G. Maggi R. Sartori G. J. Org. Chem. 1999, 64: 5004 3a Bauer T. Tetrahedron: Asymmetry 1996, 7: 981 3b Bauer T. Tetrahedron 1997, 53: 4663 4 Capet M. David F. Bertin L. Hardy J. Synth. Commun. 1995, 25: 3323 5 van Walree C. Roets M. Schuddeboom W. Jenneskens L. Verhoeven J. Warman J. Kooijman H. Spek A. J. Am. Chem. Soc. 1996, 118: 8395 6 The crystal structure has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 215036. 7 Oppolzer W. Chapuis C. Bernardinelli G. Helv. Chim. Acta 1984, 67: 1397
