Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 8
67
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

Enantioselective Synthesis of 2-Substituted Pyrrolidines from 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist rs-59022

&
Pages 1155-1166 | Received 15 Sep 1994, Published online: 23 Sep 2006

References

  • Fisher , L. E. , Caroon , J. M. , Muchowski , J. M. , Rosenkranz , R. P. and McClelland , D. L. 1991 . European Patent EP 426075 ,
  • 1991 . Chem. Abstr. , 115 : 207847
  • Fisher , L. E. , Caroon , J. M. , Clark , R. D. , Muchowski , J. M. , Rosenkranz , R. P. , McClelland , D. L. , Eglen , R. and Michel , A. Manuscript In preparation. ,
  • Gaur , S. P. , Jain , D. C. and Anand , M. 1982 . Indian J. Chem., Sect. B , 21B : 46 For a synthesis of the racemate see
  • Cooper , G. F. , McCarthy , K. E. and Martin , M. G. 1992 . Tetrahedron Lett. , 33 : 5895
  • See Meyers , A. I. and Burgess , L. E. 1992 . J. Org. Chem , 57 : 1656 and references cited therein
  • Pirkle , W. H. and Adams , P. E. 1979 . J. Org. Chem. , 44 : 2169
  • Pirkle , W. H. and Adams , P. E. 1978 . J. Org. Chem , 43 : 379
  • Solladie , G and Matloubi-Moghadam , F. 1982 . J. Org. Chem. , 47 : 91
  • Gopalan , A. , Luccero , R. , Jacobs , H. and Berryman , K. 1991 . Synth. Comm , 21 : 1321
  • Gerth , D. B. and Giese , B. 1986 . J. Org. Chem , 51 : 3726
  • Corey , E J. , Bakshi , R. K. , Shibata and Am , S. J. 1987 . Chem. Soc. , 109 : 5551
  • Review , Wallbaum , S. , Martens and Tetrahedron , J. 1992 . Asymmetry , 3 : 1992
  • Quallich , G. J. and Woodall , T. M. 1993 . Tetrahedron Lett. , 34 : 785
  • Mathre , D. J. , Jones , T. K. , Xavier , L. C. , Blacklock , T. J. , Reamer , R. A. , Mohan , J. J. and Jones , T. T. 1991 . J. Org Chem. , 56 : 751
  • Klunder , J. M. , Onami , T. and Sharpless , K. B. 1989 . J. Org. Chem. , 54 : 1295
  • Knochel , P. , Yeh , M. C. P. , Berk , S. C. and Talbert , J. 1988 . J. Org. Chem. , 53 : 2390
  • Dale , J. A. , Dull , D. L. and Mosher , H. S. 1985 . J.Am. Chem. Soc. , 107 : 2993 The enantiopurity of alcohols 2a-c was determined using 1HNMR of the corresponding MPTA esters, This high level of enantioselectivity in the CBS reduction of a ketone flanked by two methylene groups is unprecedented
  • This result implies that the nitrile function is not intrinsically responsible for the stereochemical outcome of these CBS reductions.
  • Corey , E. J. , Link , J. O. and Bakshi , R. K. 1992 . Tetrahedron Lett. , 33 : 7107
  • Jones , D. K. , Liotta , D. C. , Shinkai , I. and Mathre , D. J. 1993 . J. Org. Chem. , 58 : 799
  • Mohamadi , F. , Richards , N G.J. , Guida , W. C. , Liskamp , R. , Lipton , M. , Caufield , C. , Chang , G. , Hendrickson , T. and Still , W. C. 1990 . J. Comput. Chem , 11 : 440 In support of this argument we have conducted MM2 energy calculations for conformers A and B using MacroModel V4.5. Conformer A was determined to be 3.4 kcal/mol lower in energy than conformer BMacroModel
  • Murata , S. and Matsuda , I. 1978 . Synthesis , : 222

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.