A mild, convenient, and inexpensive method for converting imines into amines: Tin-catalyzed reduction with polymethylhydrosiloxane (PMHS)

Tetrahedron

Volumn 53, Issue 48, 1997, Pages 16349-16354

  Lopez, Rosa M ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; AMINE; IMINE; N BUTYLTRIS(2 ETHYLHEXANOATE)TIN; POLYMETHYLHYDROSILOXANE; REAGENT; UNCLASSIFIED DRUG;

CATALYSIS; CATALYST; CONFERENCE PAPER; PRIORITY JOURNAL; REDUCTION; STOICHIOMETRY;

EID: 0030730769     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01020-X     Document Type: Conference Paper

References (25)

1. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: Boston, 1987.
2. Leading references: Crich, D.; Sun, S. J. Org. Chem. 1996, 61, 7200-7201.
3. Boyer, I. J. Toxicology 1989, 55, 253-298.
4. (a) Scholl, M.; Fu, G. C. J. Org. Chem. 1994, 59, 7178-7179.
5. (b) Scholl, M.; Lim, C.-K.; Fu, G. C. J. Org. Chem. 1995, 60, 6229-6231.
6. (c) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4-5.
7. (d) Hays, D. S.; Scholl, M.; Fu, G. C. J. Org. Chem. 1996, 61, 6751-6752.
8. Other methods for reducing imines to amines: (a) Hutchins, R. O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 8, Chapter 1.2.
9. (b) Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989.
10. Earlier studies of imine reduction by silicon hydrides: (a) Frainnet, E.; Bazouin, A.; Calas, R. Compt. Rend. 1963, 257, 1304-1306.
11. (b) Loim, N. M. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1968, 1345.
12. (c) Ojima, I.; Kogure, T.; Nagai, Y. Tetrahedron Lett. 1973, 2475-2478.
13. (d) Langlois, N.; Dang, T.-P.; Kagan, H. B. Tetrahedron Lett. 1973, 4865-4868.
14. Early studies of tin-catalyzed, PMHS-mediated reduction of carbonyl groups: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96.
15. (b) Lipowitz, J.; Bowman, S. A. J. Org. Chem. 1973, 38, 162-165.
16. Gelest, Inc. (Tullytown, PA).
17. Among organotin compounds, the highest toxicity is generally observed for triorganotin species (e.g., see: Tributyltin: Case Study of an Environmental Contaminant; de Mora, S. J., Ed.; Cambridge University Press: Cambridge, UK, 1996.); diorganotin and monoorganotin compounds display successively lower toxicity (Blunden, S. J.; Cusack, P. A.; Hill, R. The Industrial Uses of Tin Chemicals; Royal Society of Chemistry: London, 1985.). The U.S. Food and Drug Administration has approved the use of 1 as a catalyst for the preparation of polyester materials that come in indirect contact with food: Federal Register, 54, 48857-48859 (November 28, 1989).
18. Among organotin compounds, the highest toxicity is generally observed for triorganotin species (e.g., see: Tributyltin: Case Study of an Environmental Contaminant; de Mora, S. J., Ed.; Cambridge University Press: Cambridge, UK, 1996.); diorganotin and monoorganotin compounds display successively lower toxicity (Blunden, S. J.; Cusack, P. A.; Hill, R. The Industrial Uses of Tin Chemicals; Royal Society of Chemistry: London, 1985.). The U.S. Food and Drug Administration has approved the use of 1 as a catalyst for the preparation of polyester materials that come in indirect contact with food: Federal Register, 54, 48857-48859 (November 28, 1989).
19. Among organotin compounds, the highest toxicity is generally observed for triorganotin species (e.g., see: Tributyltin: Case Study of an Environmental Contaminant; de Mora, S. J., Ed.; Cambridge University Press: Cambridge, UK, 1996.); diorganotin and monoorganotin compounds display successively lower toxicity (Blunden, S. J.; Cusack, P. A.; Hill, R. The Industrial Uses of Tin Chemicals; Royal Society of Chemistry: London, 1985.). The U.S. Food and Drug Administration has approved the use of 1 as a catalyst for the preparation of polyester materials that come in indirect contact with food: Federal Register, 54, 48857-48859 (November 28, 1989).
20. Aldrich Chemical Company (Milwaukee, WI).
21. Vogel's Textbook of Practical Organic Chemistry; Longman Scientific and Technical: London, 1991; pp 401-402.
22. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Pergamon Press: London, 1988; p 97.
23. Guthrie, R. D.; Burdon, L. G.; Lovell, F. L. J. Org. Chem. 1973, 38, 3114-3119.
24. Martin, G.; Guitian, E.; Castedo, L.; Saa, J. M. J. Org. Chem. 1992, 57, 5907-5911.
25. Kawakami, T.; Sugimoto, T.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1995, 60, 2677-2682.