Synthesis of α-alkoxysilanes: Birch reduction of 2-trialkylsilylfurans

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9119-9122

  Beddoes, Roy L ^a   Lewis, Mark L ^a   Gilbert, Philip ^a   Quayle, Peter ^a   Thompson, Simon P ^a   Wang, Shouming ^b   Mills, Keith ^c  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b Cantab Pharmaceuticals Ltd   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

SILANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

EID: 0030577482     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02101-6     Document Type: Article

References (31)

1. 1. Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Leiters, 1994, 35, 4183; Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Letters, 1994, 35, 4187; Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Zhao, Y.; Attwood, M. Tetrahedron Letters, 1994, 35, 4189; Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Johal, S.; Attwood, M.; Hurst, D. Tetrahedron Letters, 1995, 36, 471.
2. 1. Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Leiters, 1994, 35, 4183; Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Letters, 1994, 35, 4187; Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Zhao, Y.; Attwood, M. Tetrahedron Letters, 1994, 35, 4189; Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Johal, S.; Attwood, M.; Hurst, D. Tetrahedron Letters, 1995, 36, 471.
3. 1. Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Leiters, 1994, 35, 4183; Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Letters, 1994, 35, 4187; Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Zhao, Y.; Attwood, M. Tetrahedron Letters, 1994, 35, 4189; Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Johal, S.; Attwood, M.; Hurst, D. Tetrahedron Letters, 1995, 36, 471.
4. 1. Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Leiters, 1994, 35, 4183; Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Letters, 1994, 35, 4187; Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Zhao, Y.; Attwood, M. Tetrahedron Letters, 1994, 35, 4189; Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Johal, S.; Attwood, M.; Hurst, D. Tetrahedron Letters, 1995, 36, 471.
5. 2. Zhao, Y.; Quayle, P.; Kuo, E. A. Tetrahedron Letters, 1994, 35, 4179.
6. 3. See Kursave, D. N.; Pannes, Z. N.; Kalinkin, M. I.; Loim, N. M. in "Ionic Hydrogenation and Related Reactions." Translated by Weiner, L, OPA, Amsterdam, 1985.
7. 4. Gilbert, P, M.Sc., University of Manchester 1994; Thompson, S. P., M.Sc., University of Manchester 1995.
8. 4. Gilbert, P, M.Sc., University of Manchester 1994; Thompson, S. P., M.Sc., University of Manchester 1995.
9. 5. a. For a comprehensive review see Rabideau, P. W.; Marcinow, Z. Org. React., 1992, 42, 1;
10. b. for a timely discussion concerning the stereoselective reduction of heterocyclic systems see Donohoe, T. J.; Garg, R.; Stevenson, C. Tetrahedron:Asymmetry, 1996, 7, 317.
11. 6. Kinoshita, T.; Miyano, K.; Miwa, T. Bull. Chem. Soc. Jpn., 1975, 48, 1865.
12. 7. Kinoshita, T.; Miwa, T. Carbohydrate Research, 1973, 28, 175; Kinoshita, K.; Miwa, T. Bull. Chem. Soc. Jpn., 1978, 51, 225; Kinoshita, T.; Kinoshita, T.; Hirano, M. J. Heterocyclic Chem., 1992, 29, 1025; Hirano, M.; Yoshida, N. Synthesis, 1992, 384; Beddoes, R. L.; Lewis. M. L.; Quayle, P.; Zhao, Y; Attwood, M.; Hurst, D. Tetrahedron Letters, 1995, 36, 2641.
13. 7. Kinoshita, T.; Miwa, T. Carbohydrate Research, 1973, 28, 175; Kinoshita, K.; Miwa, T. Bull. Chem. Soc. Jpn., 1978, 51, 225; Kinoshita, T.; Kinoshita, T.; Hirano, M. J. Heterocyclic Chem., 1992, 29, 1025; Hirano, M.; Yoshida, N. Synthesis, 1992, 384; Beddoes, R. L.; Lewis. M. L.; Quayle, P.; Zhao, Y; Attwood, M.; Hurst, D. Tetrahedron Letters, 1995, 36, 2641.
14. 7. Kinoshita, T.; Miwa, T. Carbohydrate Research, 1973, 28, 175; Kinoshita, K.; Miwa, T. Bull. Chem. Soc. Jpn., 1978, 51, 225; Kinoshita, T.; Kinoshita, T.; Hirano, M. J. Heterocyclic Chem., 1992, 29, 1025; Hirano, M.; Yoshida, N. Synthesis, 1992, 384; Beddoes, R. L.; Lewis. M. L.; Quayle, P.; Zhao, Y; Attwood, M.; Hurst, D. Tetrahedron Letters, 1995, 36, 2641.
15. 7. Kinoshita, T.; Miwa, T. Carbohydrate Research, 1973, 28, 175; Kinoshita, K.; Miwa, T. Bull. Chem. Soc. Jpn., 1978, 51, 225; Kinoshita, T.; Kinoshita, T.; Hirano, M. J. Heterocyclic Chem., 1992, 29, 1025; Hirano, M.; Yoshida, N. Synthesis, 1992, 384; Beddoes, R. L.; Lewis. M. L.; Quayle, P.; Zhao, Y; Attwood, M.; Hurst, D. Tetrahedron Letters, 1995, 36, 2641.
16. 7. Kinoshita, T.; Miwa, T. Carbohydrate Research, 1973, 28, 175; Kinoshita, K.; Miwa, T. Bull. Chem. Soc. Jpn., 1978, 51, 225; Kinoshita, T.; Kinoshita, T.; Hirano, M. J. Heterocyclic Chem., 1992, 29, 1025; Hirano, M.; Yoshida, N. Synthesis, 1992, 384; Beddoes, R. L.; Lewis. M. L.; Quayle, P.; Zhao, Y; Attwood, M.; Hurst, D. Tetrahedron Letters, 1995, 36, 2641.
17. 8. Eaborn, C.; Jackson, R. A.; Pearce, R. J. Chem. Soc., Perkin Trans. 1, 1975, 2055
18. 9. a. Schultz, A. G., Kirincich, S. J., J. Org. Chem., 1996, 61, 5631; Angelaud, R.; Landais, Y. J. Org. Chem., 1996, 61, 5202;
19. 9. a. Schultz, A. G., Kirincich, S. J., J. Org. Chem., 1996, 61, 5631; Angelaud, R.; Landais, Y. J. Org. Chem., 1996, 61, 5202;
20. b. Taber, D. F.; Yet, L.; Bhamidipati, R. S. Tetrahedron Letters, 1995, 36, 351.
21. 10. Kashimura, S.; Ishifune, M.; Murai, Y.; Shono, T. Tetrahedron Letters, 1996, 37, 6737.
22. 11. Knight, D. W.; Knott, A. P. J. Chem. Soc., Perkin Trans. 1, 1981, 1125.
23. 12. Beese, G.; Keay, B. A. Synlett, 1991, 33.
24. 13. for related examples see Zhao, Y.; Quayle, P.; Kuo (née Mason), E. A. Tetrahedron Letters, 1994, 35, 3797 and refs. therein.
25. 13C nmr, ir and/or ms/combustion microanalysis. Compounds 1, 15, 16, 22 and 23 were isolated as a 2:1 mixture (trans : cis) of isomers; 2 was isolated solely as the trans isomer.
26. 15. Lewis, M. L., Ph.D., University of Manchester, 1995.
27. 16. The electrochemical oxidation of alkoxymethylsilanes is documented e.g. Yoshida, J. Topics in Current Chemistry, 1994, 170, 39. For a review of related "sila-Baeyer-Villiger" oxidations (Fleming-Tamao reaction) see Jones, G. R.; Landais, Y. Tetrahedron, 1996, 52, 7599.
28. 16. The electrochemical oxidation of alkoxymethylsilanes is documented e.g. Yoshida, J. Topics in Current Chemistry, 1994, 170, 39. For a review of related "sila-Baeyer-Villiger" oxidations (Fleming-Tamao reaction) see Jones, G. R.; Landais, Y. Tetrahedron, 1996, 52, 7599.
29. 17. For the oxidation of alkoxymethylstannanes and aminomethylstannanes using CAN see ref. 15 and Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn., 1996, 69, 2063 respectively.
30. 18. For other approaches to this ring system see Weltering, T. J.; Hoffmann, H. M. R. Tetrahedron, 1995, 57, 7389.
31. 19. For a review see Leonard, J. Contemporary Organic Synthesis, 1994, 1, 387.