New radical cascade reactions incorporating multiple one-carbon radical synthons: A versatile synthetic methodology for vicinal singly and doubly acylated oxime ethers [4]

Journal of the American Chemical Society

Volumn 121, Issue 51, 1999, Pages 12190-12191

  Ryu, Ilhyong ^a   Kuriyama, Hiroki ^a   Minakata, Satoshi ^a   Komatsu, Mitsuo ^a   Yoon, Joo Yong ^b   Kim, Sunggak ^b  

^a OSAKA UNIVERSITY   (Japan)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ETHER DERIVATIVE; OXIME; RADICAL;

CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0033616093     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992125d     Document Type: Letter

References (40)

1. For selected references, see: (a) Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 121, 1401. (b) Wasserman, H. H.; Shiraishi, M.; Coats, S. J.; Cook, J. D. Tetrahedron Lett. 1995, 3(c) Wasserman, H. H.; Lee, G. M. Tetrahedron Lett. 1994, 35, 9783. (d) Wasserman, H. H.; Blum, C. A. Tetrahedron Lett. 1994, 35, 9787. (e) Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1994, 35, 9779. (f) Wasserman, H. H.; Rotello, V. M.; Krause, G. B. Tetrahedron Lett. 1992, 33, 5419. (g) Wasserman, H. H.; Duzer, J. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 1609.
2. For selected references, see: (a) Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 121, 1401. (b) Wasserman, H. H.; Shiraishi, M.; Coats, S. J.; Cook, J. D. Tetrahedron Lett. 1995, 36, 6785. (c) Wasserman, H. H.; Lee, G. M. Tetrahedron Lett. 1994, 35, 9783. (d) Wasserman, H. H.; Blum, C. A. Tetrahedron Lett. 1994, 35, 9787. (e) Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1994, 35, 9779. (f) Wasserman, H. H.; Rotello, V. M.; Krause, G. B. Tetrahedron Lett. 1992, 33, 5419. (g) Wasserman, H. H.; Duzer, J. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 1609.
3. For selected references, see: (a) Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 121, 1401. (b) Wasserman, H. H.; Shiraishi, M.; Coats, S. J.; Cook, J. D. Tetrahedron Lett. 1995, 36, 6785. (c) Wasserman, H. H.; Lee, G. M. Tetrahedron Lett. 1994, 35, 9783. (d) Wasserman, H. H.; Blum, C. A. Tetrahedron Lett. 1994, 35, 9787. (e) Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1994, 35, 9779. (f) Wasserman, H. H.; Rotello, V. M.; Krause, G. B. Tetrahedron Lett. 1992, 33, 5419. (g) Wasserman, H. H.; Duzer, J. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 1609.
4. For selected references, see: (a) Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 121, 1401. (b) Wasserman, H. H.; Shiraishi, M.; Coats, S. J.; Cook, J. D. Tetrahedron Lett. 1995, 36, 6785. (c) Wasserman, H. H.; Lee, G. M. Tetrahedron Lett. 1994, 35, 9783. (d) Wasserman, H. H.; Blum, C. A. Tetrahedron Lett. 1994, 35, 9787. (e) Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1994, 35, 9779. (f) Wasserman, H. H.; Rotello, V. M.; Krause, G. B. Tetrahedron Lett. 1992, 33, 5419. (g) Wasserman, H. H.; Duzer, J. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 1609.
5. For selected references, see: (a) Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 121, 1401. (b) Wasserman, H. H.; Shiraishi, M.; Coats, S. J.; Cook, J. D. Tetrahedron Lett. 1995, 36, 6785. (c) Wasserman, H. H.; Lee, G. M. Tetrahedron Lett. 1994, 35, 9783. (d) Wasserman, H. H.; Blum, C. A. Tetrahedron Lett. 1994, 35, 9787. (e) Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1994, 35, 9779. (f) Wasserman, H. H.; Rotello, V. M.; Krause, G. B. Tetrahedron Lett. 1992, 33, 5419. (g) Wasserman, H. H.; Duzer, J. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 1609.
6. For selected references, see: (a) Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 121, 1401. (b) Wasserman, H. H.; Shiraishi, M.; Coats, S. J.; Cook, J. D. Tetrahedron Lett. 1995, 36, 6785. (c) Wasserman, H. H.; Lee, G. M. Tetrahedron Lett. 1994, 35, 9783. (d) Wasserman, H. H.; Blum, C. A. Tetrahedron Lett. 1994, 35, 9787. (e) Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1994, 35, 9779. (f) Wasserman, H. H.; Rotello, V. M.; Krause, G. B. Tetrahedron Lett. 1992, 33, 5419. (g) Wasserman, H. H.; Duzer, J. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 1609.
7. For selected references, see: (a) Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 121, 1401. (b) Wasserman, H. H.; Shiraishi, M.; Coats, S. J.; Cook, J. D. Tetrahedron Lett. 1995, 36, 6785. (c) Wasserman, H. H.; Lee, G. M. Tetrahedron Lett. 1994, 35, 9783. (d) Wasserman, H. H.; Blum, C. A. Tetrahedron Lett. 1994, 35, 9787. (e) Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1994, 35, 9779. (f) Wasserman, H. H.; Rotello, V. M.; Krause, G. B. Tetrahedron Lett. 1992, 33, 5419. (g) Wasserman, H. H.; Duzer, J. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 1609.
8. For a review on vicinal polycarbonyl compounds, see: Rubin, M. B. Chem. Rev. 1975, 75, 177.
9. For leading references of metal-catalyzed double vicinal carbonylations, see: (a) Ozawa, F.; Kawasaki, N.; Okamoto, H.; Yamamoto, T.; Yamamoto, A. Organometallics 1987, 6, 1640. (b) Urata, H.; Ishii, Y.; Fuchikami, T. Tetrahedron Lett. 1989, 30, 4407. (c) Yamamoto, A. Bull. Chem. Soc. Jpn. 1995, 68, 433. (d) Kayaki, Y.; Yamamoto, A. J. Synth. Org. Chem., Jpn. 1998, 56, 96.
10. For leading references of metal-catalyzed double vicinal carbonylations, see: (a) Ozawa, F.; Kawasaki, N.; Okamoto, H.; Yamamoto, T.; Yamamoto, A. Organometallics 1987, 6, 1640. (b) Urata, H.; Ishii, Y.; Fuchikami, T. Tetrahedron Lett. 1989, 30, 4407. (c) Yamamoto, A. Bull. Chem. Soc. Jpn. 1995, 68, 433. (d) Kayaki, Y.; Yamamoto, A. J. Synth. Org. Chem., Jpn. 1998, 56, 96.
11. For leading references of metal-catalyzed double vicinal carbonylations, see: (a) Ozawa, F.; Kawasaki, N.; Okamoto, H.; Yamamoto, T.; Yamamoto, A. Organometallics 1987, 6, 1640. (b) Urata, H.; Ishii, Y.; Fuchikami, T. Tetrahedron Lett. 1989, 30, 4407. (c) Yamamoto, A. Bull. Chem. Soc. Jpn. 1995, 68, 433. (d) Kayaki, Y.; Yamamoto, A. J. Synth. Org. Chem., Jpn. 1998, 56, 96.
12. For leading references of metal-catalyzed double vicinal carbonylations, see: (a) Ozawa, F.; Kawasaki, N.; Okamoto, H.; Yamamoto, T.; Yamamoto, A. Organometallics 1987, 6, 1640. (b) Urata, H.; Ishii, Y.; Fuchikami, T. Tetrahedron Lett. 1989, 30, 4407. (c) Yamamoto, A. Bull. Chem. Soc. Jpn. 1995, 68, 433. (d) Kayaki, Y.; Yamamoto, A. J. Synth. Org. Chem., Jpn. 1998, 56, 96.
13. For a review on C1 radical synthons, see: Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
14. (a) Coffman, D. D.; Pinkney, P. S.; Wall, F. T.; Wood, W. H.; Young, H. S. J. Am. Chem. Soc. 1952, 74, 3391.
15. (b) Brubaker, M. M.; Coffman, D. D.; Hoehn, H. H. J. Am. Chem. Soc. 1952, 74, 1509.
16. Also see a review on radical carbonylations: (c) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
17. To our knowledge, no kinetic information about carbonylation of acyl radicals and the reverse process has been reported.
18. For the retrosynthetic analysis of radical cascade reactions, see: Curran, D. P. Synlett 1991, 63.
19. (a) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138.
20. (b) Kim, S.; Yoon, J.-Y.; Lee, I. Y. Synlett 1997, 475.
21. (c) Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982.
22. (d) Kim, S.; Lee, I. Y. Tetrahedron Lett. 1998, 39, 1587.
23. Typical procedure: A magnetic stir bar, AIBN (17 mg, 0.1 mmol), a sulfonyl oxime ether B (207 mg, 0.7 mmol), allyltributyltin (199 mg, 0.6 mmol), an alkyl iodide 1a (123 mg, 0.5 mmol), and benzene (20 mL) were placed in a 50-mL stainless steel autoclave lined with a glass liner. The autoclave was purged with carbon monoxide, pressurized with 80 atm of CO, and heated with stirring at 90 °C for 5 h. Excess CO was discharged at room temperature. The crude mixture was washed with ether. After evaporation of the solvent, the residue was subjected to silica gel flash column chromatography (hexane/AcOEt = 19/1) to give the a-keto oxime ether 2a which contained a small amount of uncarbonylated product. Further purification by recycling by HPLC with a GPC column gave 112 mg of pure 2a (80% yield).
24. Recently Naito and co-workers reported that glycoxylic oxime ethers, analogous to 2, act as alkyl radical acceptors, see: Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174 and references therein.
25. Ryu, I.; Yamazaki, H.; Kusano, K.; Ogawa, A.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 8558.
26. For a comprehensive review on acyl radicals, see: Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
27. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
28. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin-Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
29. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
30. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
31. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
32. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
33. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
34. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
35. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
36. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
37. For leading references, see: (a) Taylor, E. C.; Lenard, K. J. Am. Chem. Soc. 1968, 90, 2424. (b) Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Seguin- Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407. (c) Taylor, E. C.; Perlman, K. L.; Kim, Y.-H.; Sword, I. P.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6413. (d) Karpetsky, T. P.; White, E. H. Tetrahedron 1973, 29, 3761. (e) Taylor, E. C.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2332. (f) Taylor, E. C.; Abdulla, R. F.; Jacobi, P. A. J. Org. Chem. 1975, 40, 2336. (g) Taylor, E. C.; Kobayashi, T. J. Org. Chem. 1976, 41, 1299. (h) Taylor, E. C.; Dumas, D. J. J. Org. Chem. 1980, 45, 2485. Also see recent applications: (i) Voegel, J. J.; Benner, S. A. Helv. Chim. Acta 1996, 79, 1863. (j) Martin, S. F.; Anderson, B. G.; Daniel, D.; Gaucher, A. Tetrahedron 1997, 53, 8997. (k) Taghavi-Moghadam, S.; Pfleiderer, W. Tetrahedron Lett. 1997, 38, 6835.
38. For recent studies for deoximation of acyl and alkoxycarbonyl oximes, see: (a) (Dess-Martin reagent) Chaudhari, S. S.; Akamanchi, K. G. Synthesis 1999, 760. (b) (Titanium trichloride) Gasparski, C. M.; Ghosh, A.; Miller, M. J. J. Org. Chem. 1992, 57, 3546.
39. For recent studies for deoximation of acyl and alkoxycarbonyl oximes, see: (a) (Dess-Martin reagent) Chaudhari, S. S.; Akamanchi, K. G. Synthesis 1999, 760. (b) (Titanium trichloride) Gasparski, C. M.; Ghosh, A.; Miller, M. J. J. Org. Chem. 1992, 57, 3546.
40. 2O (15:2:1) under un atmosphere of hydrogen for 30 min at room temperature gave a mixture of debenzylated oxime and the target tricarbonyl compound 6 as a ∼1:1 mixture in 83% total yield.