A Route to Homochiral (S)-O-Methyl Mandelic Acid and Related α-Alkoxy Carboxylic Acids from Isopropylidene Glycerol

References

• Gravas , H. , Biollaz , J. , Waeber , B. , Brunner , H. R. , Gavras , Land and Davies , R. D. 1981 . The Lancet , : 543
   PubMedGoogle Scholar
• Jurczak , J. , Pikul , S. and Bauer , T. 1986 . Tetrahedron , 42 : 447
   Web of Science ®Google Scholar
• Dumont , R. and Pfander , H. 1983 . Helv. Chim. Acta. , 66 : 814
   Web of Science ®Google Scholar
• Hirth , G. and Walther , W. 1985 . Helv. Chim. Acta. , 68 : 1863
   Web of Science ®Google Scholar
• Hagen , S. , Lawande , W. , Kilaas , L. and Anthonsen , T. 1980 . Helv. Chim. Acta. , 36 : 1301
   Google Scholar
• Anthonsen , T. , Hage , S. and Lawande , W. 1980 . Acta Chem Scand. , B-34 : 41
   Google Scholar
• Larcheveque , M. and Petit , Y. 1986 . Synthesis , 60
   Google Scholar
• Tanner , D. and Somafi , P. 1986 . Syn Comm. , : 1517
   Google Scholar
• Halebank : International Biosynthetics Ltd. . Our main supplier of (R)-1, (R)-3 and (S)-3 was
   Google Scholar
• Handa , Sheetal , Hawes , J. E. and Pryce , R. J. U. K. Patent Appl. No. 8918806.4 .
   Google Scholar
• E. P Appl. No. 413401 A2 .
   Google Scholar
• The e.e. of the acids (R)-3 and (S)-3 were determined by conversion to the dimethylamides (R)-9 and (S)-9 using conditions (a) (scheme 2) and then g. c. analysis on a WCOT fused silica capillary column coated with XE-60-S-valine-OL-phenylethylamide (50m), comparing with a racemic standard of 9. At a He flow rate of 1.5–2.0 ml min.−1, the retention time for (S)-9 was 23.55′ and or (R)-922.86′ at a column temperature of 110°C;
   Google Scholar
• same conditions as in (a) except the column temperatures 130°C for 7a, 140°C for 7b and 150°C for 7f
   Google Scholar
• as in (a) and (b) except the column temperatures were 100°C for 11d & 12d, 110°C for 11c & 12c, 140°C for 11a & 12a and 170°C for 11b & 12b;
   Google Scholar
• thus for (S)-7e, [α] D 20 = -97.78°(c0.32 in chloroform), and agrees well with that reported in reference 3g
   Google Scholar
• Results to be reported in due course
   Google Scholar
• Sato , F. , Inoue , M. , Oguro , K. and Sato , M. 1979 . Tet. Lett , 20 : 4303
   Google Scholar
• Eberle , M. K. and Kahle , G. G. 1980 . Tet. Lett. , 21 : 2303
   Google Scholar
• Chikashita , H. , Nikaya , T. , Uemura , H. and Itoh , K. 1989 . Bull. Chem. Soc. Jpn. , 62 : 2121
   Google Scholar