Highly efficient synthesis of terminal alkenes from ketones

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3047-3050

  Lebel, Hélène ^a   Guay, Danielle ^a   Paquet, Valérie ^a   Huard, Kim ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ALKENE DERIVATIVE; DIAZOMETHANE; DIOXANE; KETONE DERIVATIVE; RHODIUM; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS; WITTIG REACTION;

EID: 4544249986     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049085p     Document Type: Article

References (34)

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7. For selected examples, see: (a) Noguchi, H.; Aoyama, T.; Shioiri, T. Tetrahedron 1995, 51, 10531-10544. (b) Mehta, G.; Islam, K. Synlett 2000, 1473-1475. (c) Kim, D.; Lee, J.; Chang, J. Y.; Kim, S. Tetrahedron 2001, 57, 1247-1252. (d) Enders, D.; Voith, M. Synlett 2002, 29-32. (e) Bailey, W. F.; Daskapan, T.; Rampalli, S. J. Org. Chem. 2002, 68, 1334-1338. (f) Tanaka, M.; Imai, M.; Yamamoto, Y.; Tanaka, K.; Shimowatari, M.: Nagumo, S. J.; Kawahara, N.; Suemune, H. Org. Lett. 2003, 5, 1365-1367. (g) Pirrung, M. C.; Liu, H. Org. Lett. 2003, 5, 1983-1985. (h) Bagal, S. K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R.; Cowley, A. Org. Lett. 2003, 5, 3049-3052.
8. For selected examples, see: (a) Noguchi, H.; Aoyama, T.; Shioiri, T. Tetrahedron 1995, 51, 10531-10544. (b) Mehta, G.; Islam, K. Synlett 2000, 1473-1475. (c) Kim, D.; Lee, J.; Chang, J. Y.; Kim, S. Tetrahedron 2001, 57, 1247-1252. (d) Enders, D.; Voith, M. Synlett 2002, 29-32. (e) Bailey, W. F.; Daskapan, T.; Rampalli, S. J. Org. Chem. 2002, 68, 1334-1338. (f) Tanaka, M.; Imai, M.; Yamamoto, Y.; Tanaka, K.; Shimowatari, M.: Nagumo, S. J.; Kawahara, N.; Suemune, H. Org. Lett. 2003, 5, 1365-1367. (g) Pirrung, M. C.; Liu, H. Org. Lett. 2003, 5, 1983-1985. (h) Bagal, S. K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R.; Cowley, A. Org. Lett. 2003, 5, 3049-3052.
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10. For selected examples, see: (a) Noguchi, H.; Aoyama, T.; Shioiri, T. Tetrahedron 1995, 51, 10531-10544. (b) Mehta, G.; Islam, K. Synlett 2000, 1473-1475. (c) Kim, D.; Lee, J.; Chang, J. Y.; Kim, S. Tetrahedron 2001, 57, 1247-1252. (d) Enders, D.; Voith, M. Synlett 2002, 29-32. (e) Bailey, W. F.; Daskapan, T.; Rampalli, S. J. Org. Chem. 2002, 68, 1334-1338. (f) Tanaka, M.; Imai, M.; Yamamoto, Y.; Tanaka, K.; Shimowatari, M.: Nagumo, S. J.; Kawahara, N.; Suemune, H. Org. Lett. 2003, 5, 1365-1367. (g) Pirrung, M. C.; Liu, H. Org. Lett. 2003, 5, 1983-1985. (h) Bagal, S. K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R.; Cowley, A. Org. Lett. 2003, 5, 3049-3052.
11. For selected examples, see: (a) Noguchi, H.; Aoyama, T.; Shioiri, T. Tetrahedron 1995, 51, 10531-10544. (b) Mehta, G.; Islam, K. Synlett 2000, 1473-1475. (c) Kim, D.; Lee, J.; Chang, J. Y.; Kim, S. Tetrahedron 2001, 57, 1247-1252. (d) Enders, D.; Voith, M. Synlett 2002, 29-32. (e) Bailey, W. F.; Daskapan, T.; Rampalli, S. J. Org. Chem. 2002, 68, 1334-1338. (f) Tanaka, M.; Imai, M.; Yamamoto, Y.; Tanaka, K.; Shimowatari, M.: Nagumo, S. J.; Kawahara, N.; Suemune, H. Org. Lett. 2003, 5, 1365-1367. (g) Pirrung, M. C.; Liu, H. Org. Lett. 2003, 5, 1983-1985. (h) Bagal, S. K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R.; Cowley, A. Org. Lett. 2003, 5, 3049-3052.
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14. See also: (c) Tour, J. M.; Bedworth, P. V.; Wu, R. L. Tetrahedron Lett. 1989, 30, 3927-3930. (d) Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579-5580. (e) Lombardo, L. Org. Synth. 1987, 65, 81-89. (f) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670. (g) Nysted, L. N. U.S. Patent 3,865,848, 1975; Chem. Abstr. 1975, 83, 1406q. (h) Matsubara, S.; Sugihara, M.; Utimoto, K. Synlett 1998, 313-315.
15. See also: (c) Tour, J. M.; Bedworth, P. V.; Wu, R. L. Tetrahedron Lett. 1989, 30, 3927-3930. (d) Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579-5580. (e) Lombardo, L. Org. Synth. 1987, 65, 81-89. (f) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670. (g) Nysted, L. N. U.S. Patent 3,865,848, 1975; Chem. Abstr. 1975, 83, 1406q. (h) Matsubara, S.; Sugihara, M.; Utimoto, K. Synlett 1998, 313-315.
16. See also: (c) Tour, J. M.; Bedworth, P. V.; Wu, R. L. Tetrahedron Lett. 1989, 30, 3927-3930. (d) Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579-5580. (e) Lombardo, L. Org. Synth. 1987, 65, 81-89. (f) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670. (g) Nysted, L. N. U.S. Patent 3,865,848, 1975; Chem. Abstr. 1975, 83, 1406q. (h) Matsubara, S.; Sugihara, M.; Utimoto, K. Synlett 1998, 313-315.
17. See also: (c) Tour, J. M.; Bedworth, P. V.; Wu, R. L. Tetrahedron Lett. 1989, 30, 3927-3930. (d) Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579-5580. (e) Lombardo, L. Org. Synth. 1987, 65, 81-89. (f) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670. (g) Nysted, L. N. U.S. Patent 3,865,848, 1975; Chem. Abstr. 1975, 83, 1406q. (h) Matsubara, S.; Sugihara, M.; Utimoto, K. Synlett 1998, 313-315.
18. See also: (c) Tour, J. M.; Bedworth, P. V.; Wu, R. L. Tetrahedron Lett. 1989, 30, 3927-3930. (d) Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579-5580. (e) Lombardo, L. Org. Synth. 1987, 65, 81-89. (f) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670. (g) Nysted, L. N. U.S. Patent 3,865,848, 1975; Chem. Abstr. 1975, 83, 1406q. (h) Matsubara, S.; Sugihara, M.; Utimoto, K. Synlett 1998, 313-315.
19. See also: (c) Tour, J. M.; Bedworth, P. V.; Wu, R. L. Tetrahedron Lett. 1989, 30, 3927-3930. (d) Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579-5580. (e) Lombardo, L. Org. Synth. 1987, 65, 81-89. (f) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670. (g) Nysted, L. N. U.S. Patent 3,865,848, 1975; Chem. Abstr. 1975, 83, 1406q. (h) Matsubara, S.; Sugihara, M.; Utimoto, K. Synlett 1998, 313-315.
20. (a) Lebel, H.; Paquet, V. J. Am. Chem. Soc. 2004, 126, 320-328.
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25. This byproduct seems the result of a nucleophilic attack of triphenylphosphine onto the ketone, activated with TMSX. For a similar example, see: Lee, S. W.; Trogler, W. C. J. Org. Chem. 1990, 55, 2644-2648.
26. (a) Takeuchi, R.; Kitamura, N. New J. Chem. 1998, 22, 659-660.
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28. Oxone is known to oxidize readily organophosphorus derivatives, see: Wozniak, L. A.; Stec, W. J. Tetrahedron Lett. 1999, 40, 2637-2640.
29. It was unambiguously established that methylenetriphenylphosphorane was the active methylenation reagent formed from trimethylsilyldiazomethane, 2-propanol, and triphenylphosphine in the presence of Wilkinson's catalyst. See ref 5a for details.
30. The same amount of the phosphine reagent, either triphenylphosphine for the rhodium-catalyzed methylenation or methyltriphenylphosphonium bromide for the standard Wittig, were used to generate the same amount of the ylide reagent with both methods for comparison purpose. It is common practice however, to use an excess of methylenetriphenylphosphorane under standard Wittig reaction with such substrates to achieve better yields.
31. No cyclopropane derivative was observed in these reactions. Silylated Michael addition products (as a mixture of diastereoisomers) appear to be the major products.
32. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-13]5.
33. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D. Q.; Zhang, X. L. J. Org. Chem. 1992, 57, 2768-2771.
34. 3Br and NaHMDS: for instance, alkene 39 was isolated with 85% yield and 97% ee.