Thermal and lewis acid catalyzed intramolecular ene reactions of allenylsilanes

Synthesis

Volumn , Issue SPEC. ISS. APR., 1998, Pages 509-521

  Weinreb, Steven M ^a   Smith, Daniel T ^a   Jin, Jian ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Cycloaddition; Ene reaction; Lewis acid catalysis; Pericyclic process; Stereoselective reactions

Indexed keywords

ALLENYLSILANE; PAPUAMINE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0031776141     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-5920     Document Type: Article

References (29)

1. Borzilleri, R.M.; Weinreb, S.M.; Parvez, M. J. Am. Chem. Soc. 1994, 116, 9789.
2. Borzilleri, R.M.; Weinreb, S.M.; Parvez, M. J. Am. Chem. Soc. 1995, 117, 10905.
3. (a) Danheiser, R.L.; Carini, D.J. J. Org. Chem. 1980, 45, 3925.
4. (b) Danheiser, R.L.; Carini, D.J.; Kwasigroch, C.A. J. Org. Chem. 1986, 51, 3870.
5. (c) Danheiser, R.L.; Kwasigroch, C.A.; Tsai, Y.-M. J. Am. Chem. Soc. 1985, 107, 7233.
6. (d) Danheiser, R.L.; Stoner, E.J.; Koyama, H.; Yamashita, D.S.; Klade, C.A. J. Am. Chem. Soc. 1989, 111, 4407.
7. (e) Becker, D.A.; Danheiser, R.L. J. Am. Chem Soc. 1989, 111, 389.
8. See also: Mayr, H.; Bauml, E.; Cibura, G.; Koschinsky, R. J. Org. Chem. 1992, 57, 768.
9. For reviews of the ene reaction, see: (a) Snider, B.B. "Ene Reactions with Alkenes as Enophiles" In Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 1.
10. (b) Mikami, K; Shimizu, M. Chem. Rev. 1992, 92, 1021.
11. (c) Oppolzer, W. Angew. Chem. Int. Ed. Engl. 1984, 23, 876.
12. For a review of the carbonyl-ene reaction, see: Snider, B.B. "The Prins and Carbonyl-Ene Reactions" In Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon: Oxford, 1991; Vol. 2, p 527.
13. For a recent review of the imino-ene reaction, see: Borzilleri, R.M.; Weinreb, S.M. Synthesis 1995, 347.
14. An intermolecular imino-ene reaction involving an allene is known: Baumann, H.; Duthaler, R.O. Helv. Chim. Acta 1988, 71, 1025.
15. For preliminary accounts of portions of this work, see: Jin, J.; Smith, D.T.; Weinreb, S.M. J. Org. Chem. 1995, 60, 5366.
16. Weinreb, S.M. J. Heterocycl. Chem. 1996, 33, 1429.
17. Claus, R.E.; Schreiber, S.L. Org. Synth. 1985, 64, 150.
18. Fleming, I.; Terrett, N.K. J. Organomet. Chem. 1984, 264, 99.
19. Smith, D.T. Ph.D. Thesis, The Pennsylvania State University, 1997.
20. Jin, J. Ph.D. Thesis, The Pennsylvania State University, 1996.
21. Snider, B.B. "Alkylaluminum Halide Induced Reactions of Carbonyl Compounds with Unactivated Alkenes" In Selectivites in Lewis Acid Promoted Reactions; Schinzer, D. Ed.; Kluwer: Dordrecht, 1989; Chapter 8.
22. See also: Bertrand, M.; Roumestant, M.L.; Sylvestre-Panthet, P. Tetrahedron Lett. 1981, 22, 3589.
23. Dhokte, U.P.; Rao, A.S. Synth. Commun. 1987, 17, 355.
24. Huntsman, W.D.; Li, Y.J.; Giannamore, V.P. Isr. J. Chem. 1985, 26, 88.
25. Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.F. J. Org. Chem. 1995, 60, 863.
26. Meyer, C.; Marek, I.; Normant, J.F. Tetrahedron Lett. 1996, 37, 857.
27. Lorthiois, E.; Marek, I.; Normant, J.F. Tetrahedron Lett. 1997, 38, 89.
28. cf Snider, B.B.; Roush, D.M.; Killinger, T.A. J. Am. Chem. Soc. 1979, 101, 6023.
29. Jin, J.; Weinreb, S.M. J. Am. Chem. Soc. 1997, 119, 2050.