Selectivities in ionic reductions of alcohols and ketones with triethylsilane/trifluoroacetic acid

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 1013-1016

  Mayr, Herbert ^a   Dogan, Barbara ^b  

^a Institut fur Organische Chemie   (Germany)

^b DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; HYDROGENATION; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; REDUCTION;

EID: 0031562060     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02484-7     Document Type: Article

References (21)

1. (1) (a) Kursanov, D. N.; Parnes, Z. N.; Loim, N. M. Synthesis 1974, 633-651;
2. (b) Nagai, Y. Org. Prep. Proc. Int. 1980, 12, 13-48;
3. (c) Pawlenko, S. in Houben-Weyl, Methoden der Organischen Chemie, 4th ed.; Georg Thieme Verlag, Stuttgart 1980; Vol. XIII/5, pp 350-360;
4. (d) Hajós, A. ibid 1981, Vol. IV/1d, pp 1-486;
5. (e) Davis, A. P. ibid 1995, Vol. E21d, pp 4067-4073;
6. (f) Kursanov, D. N.; Parnes, U. N.; Kalinkin, M. I.; Loim, N. M. Ionic Hydrogenation and Related Reactions; Harwood, Chur, 1985;
7. (g) Cannon, J. G.; Kirschbaum, K. S. Synthesis 1993, 1151-1154.
8. (2) (a) Mayr, H.; Basso, N.; Hagen, G. J. Am. Chem. Soc. 1992, 114, 3060-3066;
9. (b) Mayr, H.; Patz, M. Angew. Chem. 1994,106, 990-1010;
10. Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957.
11. (3) (a) Carey, F. A.; Tremper, H. S. J. Am. Chem. Soc. 1968, 90, 2578-2583;
12. (b) West, C. T.; Donnelly, S. J.; Kooistra, D. A.; Doyle, M. P. J. Org. Chem. 1973, 38, 2675-2681;
13. (c) Doyle, M. P.; West, C. T. ibid 1975, 40, 3835-3838 and refs cited;
14. (d) Larsen, J. W.; Chang, L. W. ibid 1979, 44, 1168-1170;
15. (e) Olah, G. A.; Arvanaghi, M.; Ohannesian, L. Synthesis 1986, 770-772;
16. (f) Olah, G. A.; Wang, Q.; Prakash, G. K. S. Synlett 1992, 647-650 and references cited in ref 1.
17. (4) Mayr, H. in Cationic Polymerizations: Mechanisms, Synthesis, and Applications (Matyjaszewski, K.; Ed.), Marcel Dekker: New York, 1996, 51-136 and references cited therein.
18. 1b = 2.10 ± 0.04.
19. (6) Fukuzumi, S.; Fujita, M. Chem. Lett. 1991, 2059-2062.
20. (7) Freiberg, W. J. Prakt. Chem. 1994, 336, 565-574.
21. (8) Exner, O. Correlation Analysis of Chemical Data, Plenum Press: New York, 1988, p. 71.