Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 5
110
Views
27
CrossRef citations to date
0
Altmetric
Original Articles

Oxaziridine-Mediated Ring Expansions of Substituted Cyclobutanones: Synthesis of (-)-γ-Amino-β-Hydroxybutyric Acid (GABOB)

, , &
Pages 693-701 | Received 10 Jan 1991, Published online: 23 Sep 2006

References

  • Aubé , J. , Wang , Y. , Hammond , M. , Tanol , M. , Takusagawa , F. and Vander Velde , D. 1990 . Am J. Chem. Soc. , 112 : 4879 – 4891 .
  • Gawley , R. E. 1988 . Org. React. , 35 : 1 – 420 .
  • Bieber , L. L. 1988 . Ann. Rev. Biochem. , 57 : 261 – 283 .
  • Bahl , J. J. and Bressler , R. 1987 . Ann. Rev. Pharmacol. Toxicol. , 27 : 257 – 277 .
  • Zhou , B.-N. , Gopalan , A. S. , Van Middlesworth , F. , Shieh , W.-R. and Sih , C. J. 1983 . Am J. Chem. Soc. , 105 : 5925 – 5926 . Previous asymmetric syntheses of carnitine
  • Dropsy , E. P. and Klibanov , A. M. 1984 . Biotech. and Bioeng. , 26 : 911 – 915 .
  • Fuganti , C. and Grasselli , P. 1985 . Tetrahedron Lett. , 26 : 101 – 104 .
  • Wong , C.-H. , Drueckhammer , D. G. and Sweers , H. M. 1985 . Am J. Chem. Soc. , 107 : 4028 – 4031 .
  • Fuganti , C. , Graselli , P. , Seneci , P. F. , Servi , S. and Casati , P. 1986 . Tetrahedron Lett. , 27 : 2061 – 2062 .
  • Kitamura , M. , Ohkuma , T. , Takaya , H. and Noyori , R. 1988 . Tetrahedron Lett. , 29 : 1555 – 1556 .
  • Bellamy , F. D. , Bondoux , M. and Dodey , P. 1990 . Tetrahedron Lett. , 31 : 7323 – 7326 .
  • Kaneko , T. and Yoshida , R. 1962 . Bull. Chem. Soc. Jpn. , 35 : 1153 – 1155 .
  • Jung , M. E. and Shaw , T. J. 1980 . Am J. Chem. Soc. , 102 : 6304 – 6311 . Previous asymmetric syntheses of GABOB:
  • Bock , K. , Lundt , I. and Pederson , C. 1983 . Acta Chem. Scand. B , 37 : 341 – 344 .
  • Gopalan , A. S. and Sih , C. J. 1984 . Tetrahedron Lett. , 25 : 5235 – 5238 .
  • Rossiter , B. E. and Sharpless , K. B. 1984 . Org J. Chem. , 49 : 3707 – 3711 .
  • Rajashetekhar , B. and Kaiser , E. T. 1985 . Org J. Chem. , 50 : 5480 – 5484 .
  • Renaud , P. and Seebach , D. 1986 . Synthesis , : 424 – 426 .
  • Häusler , J. 1987 . Monatsh. Chem. , 118 : 865 – 869 .
  • Larchevéque , M. and Henrot , S. 1990 . Tetrahedron , 46 : 4277 – 4282 .
  • De Maio , D. , Madeddu , A. and Daggioli , L. 1961 . Acta Neurol. , 16 : 366
  • Colucci , W. J. , Gandour , R. D. , Fronczek , F. R. , Brady , P. S. and Brady , L. J. 1987 . J. Am. Chem. Soc. , 109 : 7915 – 7916 .
  • Petter , R. C. , Banerjee , S. and Englard , S. 1990 . Org J. Chem. , 55 : 3088 – 3097 .
  • Boyd , A. J. , Boyd , D. R. , Sharma , N. D. , Dev , K. , Jennings , W. B. and Howarth , O. W. 1989 . Chem J. Soc., Perkin Trans. 1 , : 537 – 541 . For an oxaziridine derived from a four-membered ring ketone, see
  • Ogura , K. , Yamashita , M. , Suzuki , M. , Furukawa , S. and Tsuchihashi , G. 1984 . Bull. Chem. Soc. Japan , 57 : 1637
  • Pellegata , R. , Pinza , M. and Pifferi , G. 1978 . Synthesis , : 614 – 616 .
  • Hanack , M. , Carnahan , E. J. , Krowczynski , A. , Schoberth , W. , Subramanian , L. R. and Subramanian , K. 1979 . Am J. Chem. Soc. , 101 : 100 – 108 .
  • McConnell , D. S. , Wakita , Y. , Lehto , M. E. , Schwendner , S. W. and Counsell , R. E. 199th National Meeting of the American Chemical Society . Boston, MA. Washington, D.C. : American Chemical Society . MEDI 138, Abstracts of Papers
  • Compounds 5 and 6 were prepared in the enantiomeric series opposite to that shown in the Scheme
  • For general experimental details, see reference 1
  • The stereochemistries of compounds 6a and 6b were assigned by converting them to N-unsubstituted lactams under Birch conditions. Thus, αR, 4S-6a afforded (R)-4-phenylpyrrolidin-2-one, [α]D=+37.7° (c=1.00, MeOH, mp 98–99 °C (lit.17[α]D=+40.1° (c=1.00, MeOH, mp 100–101 °C) and αR, 4R-6b afforded (R)-4-phenylpyrrolidin-2-one, [α]D=−36.6° (c=0.30, MeOH, mp 99–100 °C (lit.17 [α]D=−42.6° (c=0.30, MeOH, mp 100–101 °C). In addition, the N-unsubstituted lactams thus synthesized were shown to be optically pure (≥95% ee) by carrying out chiral solvating reagent studies using (R)-(-)-2,2,2,-trifluoro-1-(9-anthryl)ethanol.18
  • Sobocinska , M. , Zobacheva , M. M. , Perekalin , V. V. and Kupryszewski . 1979 . Pol G. Chem J. , 53 : 435 – 446 .
  • Weisman , G. R. 1983 . “Asymmetric Synthesis,” , Edited by: Morrison , J. D. Vol. 1 , 153 – 171 . Orlando : Academic Press . and references contained therein

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.