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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 15
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Original Articles

(S)-(−)-2-Methyl-2-Phenylsuccinic Anhydride, a Novel Resolving Reagent and its Application to Resolution of CIS-5-Amino-4-Phenyl-1,3-DIOXANE

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Pages 1833-1839 | Published online: 06 Dec 2006

References

  • Newman , P. 1978 . ‘Optical Resolution Procedures for Chemical Compounds’ , Vol. 1 , New York : O.R.I.C., Manhattan College .
  • Brown , E. and Violt , F. 1985 . Tetrahedron Lett. , 26 : 4451
  • Rittle , K. E. , Evans , B. E. , Bock , M. G. , Di Pardo , R. M. , Whitter , W. L. , Homnick , C. F. , Veber , D. F. and Freidinger , R. M. 1987 . Tetrahedron Lett. , 23 : 521
  • Hoeve , W. T. and Wynberg , H. 1985 . J. Org. Chem. , 50 : 4503
  • Jacques , J. , Collect , A. and Wilen , S. H. 1981 . ‘Enantio-mers, Racemates and Resolution’ , New York : Wiley Inter-science .
  • Murakmi , K. , Katsuta , N. , Takano , K. , Yamamoto , Y. , Kakegawa , T. , Saigo , K. and Nohira , H. 1979 . Nippon Kagaku Kaishi , 6 : 765 Chem. Abstr., 1979, 91, 175693j
  • Yamada , S. , Kobayashi , T. and Morinaka , Y. Japan Kokai, 74 70, 933 . Chem. Abstr., 1975, 82, 31161a
  • Meyers , A. I. , Knaus , G. , Kamata , K. and Ford , M. E. 1976 . J. Am. Chem. Soc. , 98 : 567
  • Mixture of amides (7) and (8) are separated by HPLC into a high Rf (8) (TLC Rf = 0.36, CHCl3: MeOH 80:20, 98% diastereomeric purity) and lower Rf (7) (TLC Rf = 0.30, CHCl3:MeOH 80:20, 98% diastereomeric purity) components
  • The d.e. of (7), showing [α]D = −15° (c=1 EtOH), must be 98% since the aminodioxane (-)-(1) prepared from it by heating with alkali has e.e. 98% as shown by comparing its optical rotation [α]D, = −64.9° (c=1.2 EtOH), with the rotation reported for an authentic sample5 [α]D. = −66.2° (c = 1 EtOH)
  • (S)-(+)-(3) and (R)-(-)-(4) are obtained by resolving racemic 2-methyl-2-phenylsuccinic acid with brucine and (-)-ephedrine respectively
  • A sample of (S)-(+)-(3), [α]D = + 27° (c=1 EtOH) is heated under reflux with 30% aqueous sodium hydroxide solution for 3 hr. The acid recovered (yield 98%) after the above treatment shows [α]D = + 27° (c=1 EtOH)
  • Foucaud , A. 1960 . Bull. Soc. Sci. Bretagne , 35 : 88
  • Des Abbayes , H. and Dabard , R. 1975 . Tetrahedron , 31 : 2111

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