Efficient α-alkylation and silylation of aromatic O-tert- butyldimethylsilyl ketoximes

Tetrahedron

Volumn 55, Issue 42, 1999, Pages 12275-12286

  Ortiz Marciales, Margarita ^a   De Jesús, Melvin ^a   Quiñones, Lemuel ^a   Figueroa, Dyliana ^a   Montes, Yadira L ^a   Burgos, Carlos ^a   Moctezuma, Benjamin ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

Alkyl halide; Alkylation; Benzylation; Oxime; Silicon and Compounds; Silicon Halides

Indexed keywords

1 INDANONE OXIME; 2 INDANONE OXIME; ACETOPHENONE DERIVATIVE; BENZYL BROMIDE; CHLOROTRIMETHYLSILANE; ETHYL BROMIDE; KETOXIME DERIVATIVE; METHYL IODIDE; ORGANOBROMINE DERIVATIVE; OXIME DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CAPILLARY GAS CHROMATOGRAPHY; CARBON NUCLEAR MAGNETIC RESONANCE; ISOMERISM; PRIORITY JOURNAL; TEMPERATURE;

EID: 0033570262     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00731-0     Document Type: Article

References (40)

1. a) Larock, R. C. Comprehensive Organic Transformations. A Guide to Functional Group Preparations; VCH Publishers, Inc.: New York, 1989, chapter 13, and references cited therein,
2. b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517.
3. a) Seebach, D.; Imwinkedried, R.; Weber, T. in Modern Synthetic Methods; Scheffold, R., Ed.; Spring Verlag: Berlin, 1986; Vol. 4, p 125-259.
4. b) Fuhrhop, J.; Penzlin, G. Organic Synthesis; Verlag Chemie: Weinheim, 1984.
5. a) Ager, D. J.; East., M. B. Asymmetric Synthetic Methodology; CRC Press: Boca Ratón, Fl., 1996.
6. b) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids; John Wiley and Sons, Inc.: New York, 1987.
7. c) Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Elsvier Science Ltd.: New York, 1996; Vol. 14.
8. d) Bergbreiter, D. E.; Newcomb, M. in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press Inc.: New York, 1983; Vol. 2 chapter 9.
9. a) Unterhalt, B. in Houben-Weyl Methoden der Organishen Chemie, E 14b, Part I; Klamann, D.; Hagelmann, H., Eds.: George Thieme Verlag: Stuttgart, 1990, p. 287 and references cited therein.
10. b ) Larock, R. C. Comprehensive Organic Transformations; VCH Publishers Inc.: New York, 1989; p 761-762 and references cited therein.
11. c) Hudlicky, M. in Reduction in Organic Chemistry; Ellis Horwood: Chichester, UK, 1984; p 132-133.
12. d) Reductions in Organic Synthesis; Abdel-Magid, A. F., Ed.; American Chemical Society: Washington, DC, 1996; Vol. 641.
13. (e) LeBel, N. A.; Balasubramanian, N. Tetrahedron Lett. 1986, 26, 4331.
14. f) Lednicer, D.; Mitcher, L. A. The Organic Chemistry of Drug Synthesis; Wiley Interscience: New York, 1980; Vol. 2.
15. a) Buehler, E. J. Org. Chem. 1967, 32, 261.
16. (b) Jung, M. E.; Blair, P. A.; Lowe, J. A. Tetrahedron Lett. 1976, 1439.
17. b) Hassner, A.; Nauman, F. Chem. Ber. 1988, 121, 1823.
18. a) Gawley, R. E.; Termine, E. J.; Aube, Tetrahedron Lett. 1980, 21, 3115.
19. b) Williams, D. R.; Benbow, J. Tetrahedron Lett. 1990, 31, 5881.
20. b) Ensley, H. E.; Lohr, R. Tetrahedron Lett. 1978, 1415-1418.
21. c) Spencer, T. A.; Leong, C. W. Tetrahedron Lett. 1975, 3889.
22. d) Frazer, R. R.; Dhawan, K. L. J. Chem. Soc. Chem. Commun. 1976, 674.
23. a) Ortiz-Marciales, M.; Cordera, J. F.; Pinto, S. and Alverio, I. Synthetic Commun, 1994, 24, 409.
24. b) Ortiz-Marciales, M.; Cruz, E.; Alverio, I.; Figueroa, D.; Cordero, J. F.; Morales, J.; Soto, J. A.; Dashmana, H. and Burgos, C. J. Chem. Res., (S) 1998, 10; (M) 0151.
25. b) Ortiz-Marciales, M.; Cruz, E.; Alverio, I.; Figueroa, D.; Cordero, J. F.; Morales, J.; Soto, J. A.; Dashmana, H. and Burgos, C. J. Chem. Res., (S) 1998, 10; (M) 0151.
26. c) Ortiz-Marciales, M.; Piñero L.; Ufret, L.; Algarin, W.; Morales, J. Synthetic Commun, 1998, 28, 2807.
27. a) Tillyer, R. D.; Boudreau, C.; Tschaen, D.; Dolling, U.; Reider, P. J. Tetrahedron Lett. 1995, 36, 4337.
28. b) Denmark, S. E.; Dappen, M. S. J. Org. Chem. 1984, 49, 798.
29. c) Denmark, S. E.; Dappen, M. S.; Sternberg, J. A. J. Org. Chem. 1984, 49, 4743.
30. d) Teng, M.; Fowler, F. W. Tetrahedron Lett. 1989, 30, 2481.
31. e) Behforous, M.; Gu, Z.; Stelzer, L. S.; Ahmadian, M.; Haddad, J.; Scherschel, J. A. Tetrahedron Lett. 1997, 38, 2211.
32. f) Shatzmiller, S.; Bahar, E.; Bercovici, S.; Cohen, A.; Verdoom, G. Synthesis 1990, 502.
33. Bunnelle, W. H.; Singam, P. R.; Narayanan, B. A.; Bradshaw, C. W.; Lou, S. J. Synthesis 1997, 439.
34. Mora, J.; Costa, A. Tetrahedron Lett. 1984, 25, 3493.
35. a) Palacios, F.; Aparicio, D.; De los Santos, J. M.; Rodriguez, E. Tetrahedron 1998, 54, 559.
36. b) Yanagi, R.; Matui, M.; Chinda, M.; Yamanoto, Y. Bull. Chem. Soc. Jpn. 1994, 67, 1740.
37. c) Buchanan, G. W.; Dawson, B. A. Can. J. Chem. 1978, 56, 2200.
38. d) Bunnell, C. A.; Fuch, P. L. J. Org. Chem. 1977, 42, 2614.
39. a) H. Metzger, Houben-Weyl, 3th Ed., ed. E. Miller, Thieme, Stuttgart, 1968, E 10/4, p 56.
40. (b) B. Unterhalt, Houben-Weyl, 4th Ed., ed. D. Klamann, H. Hagelmann, Thieme: Stuttgart, 1990, E14b/1, 308.