Tri-n-butyl[2-(trimethylsilyl)-ethoxymethoxymethyl]stannane: A convenient hydroxymethyl anion equivalent

Synlett

Volumn , Issue 4, 2000, Pages 455-458

  Fernández Megía, Eduardo ^a,b   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Hydroxymethylation; Lithium; Tin; Transmetallation

Indexed keywords

ANION; CARBONYL DERIVATIVE; CARBOXYL GROUP; LITHIUM; TIN;

ARTICLE; CHEMICAL STRUCTURE; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0242663103     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. (a) Peterson, D. J. Organometal. Chem. Rev. A 1972, 7, 295.
2. (b) Castro, B. Bull Soc. Chim. Fr. 1967, 1533.
3. (c) Castro, B. Bull Soc. Chim. Fr. 1967, 1540.
4. (d) Guijarro, A.; Yus, M. Tetrahedron Lett. 1993, 34, 3487.
5. (a) Knochel, P. in Organic Synthesis Highlights III, ed. Mulzer, J. and Waldmann, H.; Wiley-VCH, Weinheim, 1998, p. 67.
6. (b) Corey, E. J.; Eckrich, T. M. Tetrahedron Lett. 1983, 24, 3165.
7. (c) Lehmann, R.; Schlosser, M. Tetrahedron Lett. 1984, 25, 745.
8. For alternative methods see: (a) Boons, G. J. P. H.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1989, 30, 229.
9. (b) Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4245.
10. (c) Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4249.
11. (d) Knochel, P.; Chou, T.-S.; Chen, H. G.; Yeh, M. C. P.; Rozema, M. J. J. Org. Chem. 1989, 54, 5202.
12. (e) Chou, T.-S.; Knochel, P. J. Org. Chem. 1990, 55, 4791.
13. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481.
14. McGarvey, G. J.; Kimura, M. J. Org. Chem. 1985, 50, 4655.
15. (a) Sawyer, J. S.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1984, 106, 3376.
16. (b) Sawyer, J. S.; Kucerovy, A.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1988, 110, 842.
17. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis, Butterworths, London, 1987, p. 165-172.
18. Seebach, D.; Meyer, N. Angew. Chem. Int. Ed. Engl. 1976, 15, 438.
19. Meyer, N.; Seebach, D. Chem. Ber. 1980, 113, 1290.
20. For early examples of a-alkoxymethyllithium reagents prepared by tin-lithium exchange see ref. 2a and Schöllkopf, U. Methoden der Organischen Chemie, ed. Müller, E.; Georg Thieme Verlag, Stuttgart, 1970, vol. XIII/1, p. 133.
21. (a) Johnson, C. R.; Medich, J. R. J. Org. Chem. 1988, 53, 4131.
22. (b) Danheiser, R. L.; Gee, S. K.; Perez, J. J. J. Am. Chem. Soc. 1986, 108, 806.
23. Danheiser, R. L.; Romines, K. R.; Koyama, H.; Gee, S. K.; Johnson, C. R.; Medich, J. R. Organic Syntheses, ed. Overman, L. E.; John Wiley & Sons, New York, 1993, vol. 71, p. 133.
24. Johnson, C. R.; Medich, J. R.; Danheiser, R. L.; Romines, K. R.; Koyama, H.; Gee, S. K. Organic Syntheses, ed. Overman, L. E.; John Wiley & Sons, New York, 1993, vol. 71, p. 140.
25. Hutchinson, D. K.; Fuchs, P. L. J. Am. Chem. Soc. 1987, 109, 4930.
26. Buchwald, S. L.; Nielsen, R. B.; Dewan, J. C. Organometallics 1989, 8, 1593.
27. Li, Y.-L.; Wu, Y.-L. Tetrahedron Lett. 1996, 37, 7413.
28. Burke, S. D.; Piscopio, A. D.; Kort, M. E.; Matulenko, M. A.; Parker, M. H.; Armistead, D. M.; Shankaran, K. J. Org. Chem. 1994, 59, 332.
29. For 2 (P = EE): (a) Cai, D.; Still, W. C. J. Org. Chem. 1988, 53, 4641. For 2 (P = Bn):
30. (b) Kara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186.
31. (c) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182.
32. (d) Collum, D. B.; McDonald III, J. H.; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2120.
33. (e) Stork, G.; West, F.; Lee, H. Y.; Isaacs, R. C. A.; Manabe, S. J. Am. Chem. Soc. 1996, 118, 10660.
34. (f) McGarvey, G. J.; Mathys, J. A.; Wilson, K. J.; Overly, K. R.; Buonora, P. T.; Spoors, P. G. J. Org. Chem. 1995, 60, 7778.
35. (g) Bols, M.; Grubbe, H.; Jespersen, T. M.; Szarek, W. A. Carbohydr. Res. 1994, 253, 195. For 2 (P = MOM): see ref. 12b and
36. (h) Dufresne, C.; Gallant, M.; Gareau, Y.; Ruel, R.; Trimble, L.; Labelle, M. J. Org. Chem. 1996, 61, 8518.
37. Nemoto, H.; Matsuhashi, N.; Imaizumi, M.; Nagai, M.; Fukumoto, K. J. Org. Chem. 1990, 55, 5625. For 2 (P = PMB):
38. (j) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. J. Am. Chem. Soc. 1999, 121, 7540.
39. (k) Borthwick, A. D.; Crame, A. J.; Exall, A. M.; Weingarten, G. G. Tetrahedron Lett. 1994, 35, 7677. For 2 (P = MEM): see ref. 17. For 2 (P = BOM): see ref. 18.
40. Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
41. Antonsen, Ø.; Benneche, T.; Undheim, K. Acta Chem. Scand. 1992, 46, 757.
42. (a) Pour, M.; Negishi, E. Tetrahedron Lett. 1997, 38, 525.
43. (b) Linderman, R. J.; Ghannam, A. J. Org. Chem. 1988, 53, 2878.
44. Lipshutz, B. H.; Pegram, J. J. Tetrahedron Lett. 1980, 21, 3343.
45. Ireland, R. E.; Armstrong III, J. D.; Lebreton, J.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7152.
46. Linderman, R. J.; Godfrey, A.; Horne, K. Tetrahedron Lett. 1987, 28, 3911. (A 1,4-addition to cyclohexenone; 34-35% lower yields than the corresponding MOM and MEM counterparts).
47. Nakata, M.; Ishiyama, T.; Akamatsu, S.; Hirose, Y.; Maruoka, H.; Suzuki, R.; Tatsuta, K. Bull. Chem. Soc. Jpn. 1995, 68, 967. (Addition to a δ-lactone; 20% lower yield than the corresponding MOM counterpart).
48. (a) Weinreb amide entry 8: Williams, R. M.; Ehrlich, P. P.; Zhai, W.; Hendrix, J. J. Org. Chem. 1987, 52, 2615.
49. (b) Weinreb amide entry 9: Ley, S. V.; Cox, L. R.; Meek, G.; Metten, K.-H.; Piqué, C.; Worrall, J. M. J. Chem. Soc., Perkin Trans. 1 1997, 3299.
50. 2EtN, DMF, 90°C, 24 h, 96%).
51. Larchevêque, M.; Debal, A.; Cuvigny, T. Bull. Soc. Chim. Fr. 1974, 1710.