Regioselective directed lithiation of N-Boc 3-hydroxypyrrolidine. Synthesis of 2-substituted 4-hydroxypyrrolidines

Chemical Communications

Volumn , Issue 16, 1998, Pages 1723-1724

  Sunose, Mihiro ^a   Peakman, Torren M ^a   Charmant, Jonathan P H ^a   Gallagher, Timothy ^a   Macdonald, Simon J F ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037925661     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804211j     Document Type: Article

References (17)

1. P. Beak, A. Basu, D. J. Gallagher, Y. S. Park and S. Thayumanavan, Acc. Chem. Res., 1996, 29, 552;
2. M. Gray, M. Tinkl and V. Snieckus, in Comprehensive Organometallic Chemistry, ed. E. W. Abel and F. G. A. Stone, Elsevier, New York, vol. 11, ch. 1;
3. P. Beak, W. J. Zajdel and D. B. Reitz, Chem. Rev., 1984, 84, 471.
4. D. L. Comins and M. A. Weglarz, J. Org. Chem., 1988, 53, 4437;
5. for a recent example involving a desymmetrisation process, see M. Lautens, E. Fillion and M. Sampat, J. Org. Chem., 1997, 62, 7080.
6. Steric factors also play a role in determining regiochemical control in spite of the presence of a (sulfur-based) directing group, see D. J. Hart, J. Li, W.-L. Wu and A. P. Kozikowski, J. Org. Chem., 1997, 62, 5023.
7. M. Giles, M. S. Hadley and T. Gallagher, J. Chem. Soc., Chem. Commun., 1990, 831.
8. P. Beak and W. K. Lee, J. Org. Chem., 1993, 58, 1109.
9. V. Wittmann and H. Kessler, Angew. Chem., Int. Ed. Engl., 1993, 32, 1091;
10. P. Lesimple and J.-M. Beau, Bioorg. Med. Chem., 1994, 2, 1319;
11. O. Frey, M. Hoffmann, V. Wittmann, H. Kessler, P. Uhlmann and A. Vasella, Helv. Chim. Acta, 1994, 77, 2060;
12. D. Mazeas, T. Skrydstrup and J.-M. Beau, Angew. Chem., Int. Ed. Engl., 1994, 33, 1383;
13. M. Hoffmann and H. Kessler, Tetrahedron Lett., 1994, 35, 6067;
14. D. Urban, T. Skrydstrup, C. Riche, A. Chiaroni and J.-M. Beau, Chem. Commun., 1996, 1883.
15. For a review of carbohydrate-based Cl nucleophiles, see J.-M. Beau and T. Gallagher, Top. Curr. Chem., 1997, 87, 1.
16. G. Pandey and D. Chakrabarti, Tetrahedron Lett., 1996, 37, 2285.
17. D. A. Fletcher, R. F. McMeeking and D. J. Parkin, J. Chem. Inf. Comput. Sci., 1996, 36, 746.