Scope of the intramolecular imidotitanium-alkyne [2 + 2] cycloaddition-azatitanetine acylation sequence. An efficient procedure for the synthesis of 2-(2-keto-1-alkylidene)tetrahydropyrroles and related compounds

Organometallics

Volumn 16, Issue 8, 1997, Pages 1523-1525

  Fairfax, David ^a   Stein, Matthias ^a   Livinghouse, Tom ^a   Jensen, Michael ^a  

^a MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003188239     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om961074f     Document Type: Article

References (18)

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3. (c) Negishi, E.-i.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404.
4. (a) Boese, R.; Harvey, D. F.; Malaska, M. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1994, 116, 11153.
5. (b) Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
6. (c) Padwa, A.; Sandanayaka, V. P.; Curtis, E. A. J. Am. Chem. Soc. 1994, 116, 2667.
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9. (a) McGrane, P. L.; Jensen, M. D.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
10. (b) For the use of various di(cyclopentadienyl) lanthanide complexes in catalytic aminoalkyne cyclizations, see: Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295 and references therein.
11. (a) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485.
12. (b) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323.
13. Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z.-i. J. Am. Chem. Soc. 1988, 110, 3994.
14. Cardoso, A. M.; Clark, R. J. H.; Moorhouse, S. J. Chem. Soc. Dalton Trans. 1980, 1156.
15. Lund, E. C.; Livinghouse, T. Organometallics 1990, 9, 2426.
16. 1-pyrrolines occurred during the standard work-up procedure.
17. For an early and suggestive example of azatitanetine cyanoalkylidenation, see ref 7a.
18. Jensen, M. D. Ph.D. Dissertation, University of Minnesota, Minneapolis, MN, 1991.