Metal-catalyzed reaction of indoline diazoamides possessing a C-2 CH2X substituent: Site-selectivity, diastereoselectivity, and chemoselectivity

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2897-2900

  Wee, Andrew G H ^a   Slobodian, J ^a  

^a UNIVERSITY OF REGINA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042228528     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951320h     Document Type: Article

References (25)

1. Wee, A. G. H.; Liu, B,-S.; Zhang, L. J. Org. Chem. 1992, 57, 4404.
2. Some recent approaches, see for example: (a) Cotterill, A. S.; Hartopp, P.; Jones, G. B.; Moody, C. J.; Norton, C. L.; O'Sullivan, N. O.; Swann, E. Tetrahedron 1994, 50, 7657. (b) Ziegler, F. E,; Belema, M. J. Org. Chem. 1994, 59, 7962. (c) Michael, J. P.; Chang, S.-F.; Wilson, C. F. Tetrahedron Lett. 1993, 34, 8365. (d) Vedejs, E.; Piotrowski, D. W. J. Org. Chem. 1993, 58, 1341. (e) Shiue, J.-S.; Fang, J.-M. J. Chem. Soc., Chem. Commun. 1993, 1277. Review of earlier approaches see: Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1986, 105, 199.
3. Some recent approaches, see for example: (a) Cotterill, A. S.; Hartopp, P.; Jones, G. B.; Moody, C. J.; Norton, C. L.; O'Sullivan, N. O.; Swann, E. Tetrahedron 1994, 50, 7657. (b) Ziegler, F. E,; Belema, M. J. Org. Chem. 1994, 59, 7962. (c) Michael, J. P.; Chang, S.-F.; Wilson, C. F. Tetrahedron Lett. 1993, 34, 8365. (d) Vedejs, E.; Piotrowski, D. W. J. Org. Chem. 1993, 58, 1341. (e) Shiue, J.-S.; Fang, J.-M. J. Chem. Soc., Chem. Commun. 1993, 1277. Review of earlier approaches see: Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1986, 105, 199.
4. Some recent approaches, see for example: (a) Cotterill, A. S.; Hartopp, P.; Jones, G. B.; Moody, C. J.; Norton, C. L.; O'Sullivan, N. O.; Swann, E. Tetrahedron 1994, 50, 7657. (b) Ziegler, F. E,; Belema, M. J. Org. Chem. 1994, 59, 7962. (c) Michael, J. P.; Chang, S.-F.; Wilson, C. F. Tetrahedron Lett. 1993, 34, 8365. (d) Vedejs, E.; Piotrowski, D. W. J. Org. Chem. 1993, 58, 1341. (e) Shiue, J.-S.; Fang, J.-M. J. Chem. Soc., Chem. Commun. 1993, 1277. Review of earlier approaches see: Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1986, 105, 199.
5. Some recent approaches, see for example: (a) Cotterill, A. S.; Hartopp, P.; Jones, G. B.; Moody, C. J.; Norton, C. L.; O'Sullivan, N. O.; Swann, E. Tetrahedron 1994, 50, 7657. (b) Ziegler, F. E,; Belema, M. J. Org. Chem. 1994, 59, 7962. (c) Michael, J. P.; Chang, S.-F.; Wilson, C. F. Tetrahedron Lett. 1993, 34, 8365. (d) Vedejs, E.; Piotrowski, D. W. J. Org. Chem. 1993, 58, 1341. (e) Shiue, J.-S.; Fang, J.-M. J. Chem. Soc., Chem. Commun. 1993, 1277. Review of earlier approaches see: Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1986, 105, 199.
6. Some recent approaches, see for example: (a) Cotterill, A. S.; Hartopp, P.; Jones, G. B.; Moody, C. J.; Norton, C. L.; O'Sullivan, N. O.; Swann, E. Tetrahedron 1994, 50, 7657. (b) Ziegler, F. E,; Belema, M. J. Org. Chem. 1994, 59, 7962. (c) Michael, J. P.; Chang, S.-F.; Wilson, C. F. Tetrahedron Lett. 1993, 34, 8365. (d) Vedejs, E.; Piotrowski, D. W. J. Org. Chem. 1993, 58, 1341. (e) Shiue, J.-S.; Fang, J.-M. J. Chem. Soc., Chem. Commun. 1993, 1277. Review of earlier approaches see: Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1986, 105, 199.
7. Some recent approaches, see for example: (a) Cotterill, A. S.; Hartopp, P.; Jones, G. B.; Moody, C. J.; Norton, C. L.; O'Sullivan, N. O.; Swann, E. Tetrahedron 1994, 50, 7657. (b) Ziegler, F. E,; Belema, M. J. Org. Chem. 1994, 59, 7962. (c) Michael, J. P.; Chang, S.-F.; Wilson, C. F. Tetrahedron Lett. 1993, 34, 8365. (d) Vedejs, E.; Piotrowski, D. W. J. Org. Chem. 1993, 58, 1341. (e) Shiue, J.-S.; Fang, J.-M. J. Chem. Soc., Chem. Commun. 1993, 1277. Review of earlier approaches see: Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1986, 105, 199.
8. Knittel, D. Synthesis 1985, 186.
9. We found that reaction temperature (rt vs reflux) had no influence on the diastereoselectivity and the chemoselectivity (C-H insertion versus O-interception) of the reaction.
10. (a) Exo and endo refers to the orientation of X with respect to the convex side of tricyclic ring: exo = β-orietation and endo = α-orientation; cis and trans refer to the relative stereochemistry of X and R′ at C-1 and C-2 (pyrrolo[1,2-α]indole numbering), respectively. We thank a referee for bringing this designation to our attention. (b) The assignment of the relative stereochemistries at C-1, C-2, and C-9a was based on results obtained from difference NOE experiments performed on EX-t, EX-c, and EN-t-12a,b.
11. Krapcho, A. P. Synthesis 1982, 893.
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16. (b) Taber, D. F.; Saleh, S. A.; Korsmeyer, R. W. J. Org. Chem. 1980, 45, 4699. For a review on copper-catalyzed reactions: Burke, S. D.; Grieco, P. A. Org. React. (N.Y.) 1979, 26, 361. See also Ye, T.; McKervey, M. A. Chem Rev. 1994, 94, 1091.
17. (b) Taber, D. F.; Saleh, S. A.; Korsmeyer, R. W. J. Org. Chem. 1980, 45, 4699. For a review on copper-catalyzed reactions: Burke, S. D.; Grieco, P. A. Org. React. (N.Y.) 1979, 26, 361. See also Ye, T.; McKervey, M. A. Chem Rev. 1994, 94, 1091.
18. (b) Taber, D. F.; Saleh, S. A.; Korsmeyer, R. W. J. Org. Chem. 1980, 45, 4699. For a review on copper-catalyzed reactions: Burke, S. D.; Grieco, P. A. Org. React. (N.Y.) 1979, 26, 361. See also Ye, T.; McKervey, M. A. Chem Rev. 1994, 94, 1091.
19. Recently, Lim and Sulikowski showed that copper carbenoids efficiently partake in C-H insertion reactions in α-(2-pyrrolidinophenyl)-α-diazoacetates wherein the carbenoid carbon and the C-H insertion site are held in close proximity. Sulikowski, G.; Lim, H.-J. J. Org. Chem. 1995, 60, 2326.
20. (a) Clark, J. S.; Krowiak, S. A.; Street, L. J. Tetrahedron Lett. 1993, 34, 4385.
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23. For an example of an interception of a carbene, generated under phase transfer reaction conditions, by an azide group see: Szonyi, F.; Cambon, A. Tetrahedron Lett. 1992, 33, 2339.
24. (a) For a review: Padwa, A.; Hornbuckle, S. F. 1991, 91, 263.
25. (b) A review of earlier work on [2,3]-Wittig rearrangement of sulfonium ylides see: Ando, W. Acc. Chem. Res. 1977, 10, 179.