A new method for the one-step synthesis of α,β-unsaturated carbonyl systems from saturated alcohols and carbonyl compounds [3]

Journal of the American Chemical Society

Volumn 122, Issue 31, 2000, Pages 7596-7597

  Nicolaou, K C ^a   Zhong, Y L ^b   Baran, P S ^b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE;

CHEMICAL REACTION; LETTER; SYNTHESIS; TECHNIQUE;

EID: 0034625897     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001825b     Document Type: Letter

References (17)

1. For a review of halogenation-dehydrohalogenation reactions and sulfur-, selenium-, and palladium-based methods for oxidation adjacent to the C=O bond, see: Buckle, D. R.; Pinto, I. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 7, pp 119-146.
2. For a comprehensive list of these reagents, see: Larock, R. C. Comprehensive Organic Transformations; John Wiley & Sons: New York, 1999; pp. 251-256. See also: Nicolaou, K. C.; Petasis, N. A. Selenium in Natural Products Synthesis; CIS, Inc.: Philadelphia, 1984; Chapter 3.
3. For a comprehensive list of these reagents, see: Larock, R. C. Comprehensive Organic Transformations; John Wiley & Sons: New York, 1999; pp. 251-256. See also: Nicolaou, K. C.; Petasis, N. A. Selenium in Natural Products Synthesis; CIS, Inc.: Philadelphia, 1984; Chapter 3.
4. See: (a) refs 1 and 2. (b) Ito, Y.; Hirato, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011-1013.
5. See: (a) refs 1 and 2. (b) Ito, Y.; Hirato, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011-1013.
6. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 622-625. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 625-628. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525-2529.
7. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 622-625. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 625-628. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525-2529.
8. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 622-625. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 625-628. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525-2529.
9. First preparation of IBX: Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727. For a superior route to IBX, see: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. Introduction of the acronym "IBX": Katritzky, A. R.; Duell, B. L.; Gallos, J. K. Org. Magn. Reson. 1989, 27, 1007-1011. Use as a selective oxidant for alcohols: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022. Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485-3488.
10. First preparation of IBX: Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727. For a superior route to IBX, see: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. Introduction of the acronym "IBX": Katritzky, A. R.; Duell, B. L.; Gallos, J. K. Org. Magn. Reson. 1989, 27, 1007-1011. Use as a selective oxidant for alcohols: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022. Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485-3488.
11. First preparation of IBX: Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727. For a superior route to IBX, see: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. Introduction of the acronym "IBX": Katritzky, A. R.; Duell, B. L.; Gallos, J. K. Org. Magn. Reson. 1989, 27, 1007-1011. Use as a selective oxidant for alcohols: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022. Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485-3488.
12. First preparation of IBX: Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727. For a superior route to IBX, see: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. Introduction of the acronym "IBX": Katritzky, A. R.; Duell, B. L.; Gallos, J. K. Org. Magn. Reson. 1989, 27, 1007-1011. Use as a selective oxidant for alcohols: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022. Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485-3488.
13. First preparation of IBX: Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727. For a superior route to IBX, see: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. Introduction of the acronym "IBX": Katritzky, A. R.; Duell, B. L.; Gallos, J. K. Org. Magn. Reson. 1989, 27, 1007-1011. Use as a selective oxidant for alcohols: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022. Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485-3488.
14. For the use of benzeneseleninic anhydride in refluxing PhCl to perform similar oxidations in steroidal systems, see: (a) Barton, D. H. R.; Brewster, A. G.; Hui, R. A. H. F.; Lester, D. J.; Ley, S. V.; Back, T. G. J. Chem. Soc., Chem. Commun. 1978, 952-954. (b) Barton, D. H. R.; Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Ley, S. V. J. Chem. Soc., Perkin Trans 1 1982, 1947-1952.
15. For the use of benzeneseleninic anhydride in refluxing PhCl to perform similar oxidations in steroidal systems, see: (a) Barton, D. H. R.; Brewster, A. G.; Hui, R. A. H. F.; Lester, D. J.; Ley, S. V.; Back, T. G. J. Chem. Soc., Chem. Commun. 1978, 952-954. (b) Barton, D. H. R.; Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Ley, S. V. J. Chem. Soc., Perkin Trans 1 1982, 1947-1952.
16. 4 with IBX reactions under similar conditions it is surmised that silyl ether, acetate, benzoate, acetal, and p-methoxyphenyl groups are stable under the reaction conditions employed in the present process.
17. Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 44-122.