Reaction of propargylsilanes with chromium carbene complexes: Synthesis of conjugated diene enol ethers through a tandem alkyne insertion-1,2-silicon shift process

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4500-4501

  Herndon, James W ^a   Patel, Paren P ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010325502     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960654j     Document Type: Article

References (13)

1. For recent references, see: Macomber, D. W.; Madhukar, P.; Rogers, R. D. Organometallics 1992, 10, 2121-2128.
2. For a recent review of carbene complexes, see: Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1065-1113.
3. Similar 1,2-alkyl shifts of electrophilic carbene complexes are well-documented. (a) Bly, R. S.; Bly, R. K.; Hossain, M. M.; Lebioda, L.; Raja, M. J. Am. Chem. Soc. 1988, 110, 7723-7730. (b) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699-701.
4. Similar 1,2-alkyl shifts of electrophilic carbene complexes are well-documented. (a) Bly, R. S.; Bly, R. K.; Hossain, M. M.; Lebioda, L.; Raja, M. J. Am. Chem. Soc. 1988, 110, 7723-7730. (b) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699-701.
5. For a recent example of benzannulation using arylcarbene complexes and alkynes, see: Bao, J.; Wulff, W. D.; Fumo, M. J.; Grant, E. B.; Heller, D. P.; Whitcomb, M.C.; Yeung, S.-M. J. Am. Chem. Soc. 1996, 118, 2166-2181.
6. For five-membered ring annulation using cyclopropylcarbene complexes and alkynes, see: Tumer, S. U.; Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1992, 114, 8394-8404.
7. (a) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736-744.
8. (b) Söderberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113-3121.
9. Strobel, P.; Andrieu, C. G.; Paquer, D.; Vazeaux, M.; Pham, C. C. Nouv. J. Chim. 1980, 44, 101-107.
10. McCallum, J. S.; Kunng, F.-A.; Gilbertson, S. R.; Wulff, W. D. Organometallics 1988, 7, 2346-2360.
11. Ehlinger, E.; Magnus, P. J. Am. Chem. Soc. 1980, 102, 5004-5011.
12. (a) Söderberg, B. C.; Turbeville, D. M. Organometallics 1991, 10, 3951-3953.
13. (b) Harvey, D. F.; Neil, D. A. Tetrahedron 1993, 49, 2145-2150.