New and stereospecific synthesis of allenes in a single step from propargylic alcohols

Journal of the American Chemical Society

Volumn 118, Issue 18, 1996, Pages 4492-4493

  Myers, Andrew G ^a   Zheng, Bin ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE;

ARTICLE; CHROMATOGRAPHY; DRUG SYNTHESIS; DRUG TRANSFORMATION; NONHUMAN; ORGANIC CHEMISTRY; PURIFICATION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 15844409635     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960443w     Document Type: Article

References (25)

1. Reviews: (a) Rossi, R.; Diversi, P. Synthesis 1973, 25. (b) The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Wiley New York, 1980. The Chemisiry of the Allenes; Landor, S. R., Ed.: Academic Press: London, 1982. (d) Coppola, G. M.; Schuster, H. F. Allenes in Organic Synthesis, Wiley: New York, 1984. (e) Pasto, D. J. Tetrahedron 1984, 40, 2805. For leading references into the preparation and synthetic utility of the important (trialkylsilyl)allenes, see: (f) Danheiser, R. L.; Tsai, Y.-M.; Fink, D. M. Org. Synth. 1988, 66, 1. (g) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407.
2. Reviews: (a) Rossi, R.; Diversi, P. Synthesis 1973, 25. (b) The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Wiley New York, 1980. The Chemisiry of the Allenes; Landor, S. R., Ed.: Academic Press: London, 1982. (d) Coppola, G. M.; Schuster, H. F. Allenes in Organic Synthesis, Wiley: New York, 1984. (e) Pasto, D. J. Tetrahedron 1984, 40, 2805. For leading references into the preparation and synthetic utility of the important (trialkylsilyl)allenes, see: (f) Danheiser, R. L.; Tsai, Y.-M.; Fink, D. M. Org. Synth. 1988, 66, 1. (g) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407.
3. Reviews: (a) Rossi, R.; Diversi, P. Synthesis 1973, 25. (b) The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Wiley New York, 1980. (c) The Chemisiry of the Allenes; Landor, S. R., Ed.: Academic Press: London, 1982. (d) Coppola, G. M.; Schuster, H. F. Allenes in Organic Synthesis, Wiley: New York, 1984. (e) Pasto, D. J. Tetrahedron 1984, 40, 2805. For leading references into the preparation and synthetic utility of the important (trialkylsilyl)allenes, see: (f) Danheiser, R. L.; Tsai, Y.-M.; Fink, D. M. Org. Synth. 1988, 66, 1. (g) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407.
4. Reviews: (a) Rossi, R.; Diversi, P. Synthesis 1973, 25. (b) The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Wiley New York, 1980. The Chemisiry of the Allenes; Landor, S. R., Ed.: Academic Press: London, 1982. (d) Coppola, G. M.; Schuster, H. F. Allenes in Organic Synthesis, Wiley: New York, 1984. (e) Pasto, D. J. Tetrahedron 1984, 40, 2805. For leading references into the preparation and synthetic utility of the important (trialkylsilyl)allenes, see: (f) Danheiser, R. L.; Tsai, Y.-M.; Fink, D. M. Org. Synth. 1988, 66, 1. (g) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407.
5. Reviews: (a) Rossi, R.; Diversi, P. Synthesis 1973, 25. (b) The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Wiley New York, 1980. The Chemisiry of the Allenes; Landor, S. R., Ed.: Academic Press: London, 1982. (d) Coppola, G. M.; Schuster, H. F. Allenes in Organic Synthesis, Wiley: New York, 1984. (e) Pasto, D. J. Tetrahedron 1984, 40, 2805. For leading references into the preparation and synthetic utility of the important (trialkylsilyl)allenes, see: (f) Danheiser, R. L.; Tsai, Y.-M.; Fink, D. M. Org. Synth. 1988, 66, 1. (g) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407.
6. Reviews: (a) Rossi, R.; Diversi, P. Synthesis 1973, 25. (b) The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Wiley New York, 1980. The Chemisiry of the Allenes; Landor, S. R., Ed.: Academic Press: London, 1982. (d) Coppola, G. M.; Schuster, H. F. Allenes in Organic Synthesis, Wiley: New York, 1984. (e) Pasto, D. J. Tetrahedron 1984, 40, 2805. For leading references into the preparation and synthetic utility of the important (trialkylsilyl)allenes, see: (f) Danheiser, R. L.; Tsai, Y.-M.; Fink, D. M. Org. Synth. 1988, 66, 1. (g) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407.
7. Reviews: (a) Rossi, R.; Diversi, P. Synthesis 1973, 25. (b) The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Wiley New York, 1980. The Chemisiry of the Allenes; Landor, S. R., Ed.: Academic Press: London, 1982. (d) Coppola, G. M.; Schuster, H. F. Allenes in Organic Synthesis, Wiley: New York, 1984. (e) Pasto, D. J. Tetrahedron 1984, 40, 2805. For leading references into the preparation and synthetic utility of the important (trialkylsilyl)allenes, see: (f) Danheiser, R. L.; Tsai, Y.-M.; Fink, D. M. Org. Synth. 1988, 66, 1. (g) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407.
8. Myers, A. G.; Finney, N. S., Kuo, E. Y. Tetrahedron Lett. 1989, 30, 5747.
9. Unpublished results; desilylation is observed.
10. (a) Mitsunobu, O. Synthesis 1981, 1.
11. (b) Hughes, D. L. Org. React. 1992, 42, 335.
12. 2) are incompatible with the Mitsunobu reaction.
13. 2) are incompatible with the Mitsunobu reaction.
14. 2) are incompatible with the Mitsunobu reaction.
15. (a) Myers, A. G.; Kukkola, P. J. J. Am. Chem. Soc. 1990, 112, 8208. Prior to this work, Corey et al. had developed a method for reductive allylic transposition based on the air-oxidation of an allvlic hydrazine: (b) Corey, E. J.; Wess, G.; Xiang, Y. B.; Singh, A. K. J. Am. Chem. Soc. 1987, 109, 4717.
16. (a) Myers, A. G.; Kukkola, P. J. J. Am. Chem. Soc. 1990, 112, 8208. Prior to this work, Corey et al. had developed a method for reductive allylic transposition based on the air-oxidation of an allvlic hydrazine: (b) Corey, E. J.; Wess, G.; Xiang, Y. B.; Singh, A. K. J. Am. Chem. Soc. 1987, 109, 4717.
17. 1-Allyl-1-sulfonylhydrazines have been prepared by base-promoted alkylation, and their fragmentation has been induced by heating (60°C) in acetic acid: (a) Sato, T.; Homma, I. Bull. Chem. Soc. Jpn. 1971, 44, 1885. (b) Corey, E. J : Cane, D. E.; Libit, L. J. Am. Chem. Soc. 1971, 93, 7016. 1-Alkyl-1-sulfonylhydrazines have been prepared and fragmented in situ by the amination of sulfonamides with chloramine in refluxing THF in the presence of hydroxide: (c) Nickon, A.; Hill, A. S. J. Am. Chem. Soc. 1964, 86, 1152. (d) Guziec, F. S., Jr.; Wei, D. J. Org. Chem. 1992, 57, 3772.
18. 1-Allyl-1-sulfonylhydrazines have been prepared by base-promoted alkylation, and their fragmentation has been induced by heating (60°C) in acetic acid: (a) Sato, T.; Homma, I. Bull. Chem. Soc. Jpn. 1971, 44, 1885. (b) Corey, E. J : Cane, D. E.; Libit, L. J. Am. Chem. Soc. 1971, 93, 7016. 1-Alkyl-1-sulfonylhydrazines have been prepared and fragmented in situ by the amination of sulfonamides with chloramine in refluxing THF in the presence of hydroxide: (c) Nickon, A.; Hill, A. S. J. Am. Chem. Soc. 1964, 86, 1152. (d) Guziec, F. S., Jr.; Wei, D. J. Org. Chem. 1992, 57, 3772.
19. 1-Allyl-1-sulfonylhydrazines have been prepared by base-promoted alkylation, and their fragmentation has been induced by heating (60°C) in acetic acid: (a) Sato, T.; Homma, I. Bull. Chem. Soc. Jpn. 1971, 44, 1885. (b) Corey, E. J : Cane, D. E.; Libit, L. J. Am. Chem. Soc. 1971, 93, 7016. 1-Alkyl-1-sulfonylhydrazines have been prepared and fragmented in situ by the amination of sulfonamides with chloramine in refluxing THF in the presence of hydroxide: (c) Nickon, A.; Hill, A. S. J. Am. Chem. Soc. 1964, 86, 1152. (d) Guziec, F. S., Jr.; Wei, D. J. Org. Chem. 1992, 57, 3772.
20. 1-Allyl-1-sulfonylhydrazines have been prepared by base-promoted alkylation, and their fragmentation has been induced by heating (60°C) in acetic acid: (a) Sato, T.; Homma, I. Bull. Chem. Soc. Jpn. 1971, 44, 1885. (b) Corey, E. J : Cane, D. E.; Libit, L. J. Am. Chem. Soc. 1971, 93, 7016. 1-Alkyl-1-sulfonylhydrazines have been prepared and fragmented in situ by the amination of sulfonamides with chloramine in refluxing THF in the presence of hydroxide: (c) Nickon, A.; Hill, A. S. J. Am. Chem. Soc. 1964, 86, 1152. (d) Guziec, F. S., Jr.; Wei, D. J. Org. Chem. 1992, 57, 3772.
21. Hunig, S., Müller, H. R.; Thier, W. Angew. Chem., Int. Ed. Engl. 1965, 4, 271.
22. Dann, A. T.; Davies, W. J. Chem. Soc. 1929, 1050.
23. 3P (170 mg, 0.65 mmol, 1.3 equiv) in THF (2 mL) at -15°C. After 10 min, a solution of 1-dimethylanuno-2-heptyn-4-ol (78 mg. 0.50 mmol. 1 equiv) in THF (1.5 mL) was added to the yellow reaction mixture, followed 10 min later by a solution of NBSH (0.14 g, 0.65 mmol, 1.3 equiv) in THF (2.0 mL). The resulting suspension was held at -15°C for 1 h, after which time TLC analysis indicated complete consumption of the starting alcohol. The reaction mixture was warmed to 23°C and allowed to stand overnight (8 h). Concentration of the reaction mixture and purification of the residue by Chromatography on silica gel afforded the title allene as a colorless oil (57 mg, 83%).
24. (a) Danheiser, R. L.; Carini, D. J.; Fink, D. M.; Basak, A. Tetrahedron, 1983, 39, 935
25. (b) Hopf, H.; Naujoks, E. Tetrahedron Lett. 1988, 29, 609.