3-arylpropanoate esters through the palladium-catalyzed reaction of aryl halides with acrolein diethyl acetal

Synlett

Volumn , Issue 8, 2003, Pages 1133-1136

  Battistuzzi, Gianfranco ^a   Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Bernini, Roberta ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF TUSCIA   (Italy)

Author keywords

Alkenes; Aryl halides; Esters; Heck reaction; Palladium

Indexed keywords

ACROLEIN DERIVATIVE; ACROLEIN DIETHYL ACETAL; ALDEHYDE; BROMINE DERIVATIVE; ESTER; ETHER; FUNCTIONAL GROUP; HALIDE; IODINE DERIVATIVE; KETONE; NITRILE; NITRO DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPIONIC ACID DERIVATIVE; PROPIONIC ACID ESTER; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; SYNTHESIS; TEMPERATURE;

EID: 0038391485     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39900     Document Type: Article

References (48)

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3. For related syntheses of α,β-unsaturated aldehydes based on the palladium-catalyzed reaction of aryl halides with a three carbon partner, see: (a) Patel, B. A.; Kim, J.-I.; Bender, D. D.; Kao, L.-C.; Heck, R. F. J. Org. Chem. 1981, 46, 1061. (b) Jeffery, T. J. J. Chem. Soc., Chem. Commun. 1984, 1287. (c) Unroe, M. R.; Reinhardt, B. A. Synthesis 1987, 981. (d) Parrain, J.-L.; Duchene, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187. (e) Phuan, P.-W.; Kozlowski, M. C. Tetrahedron Lett. 2001, 42, 3963.
4. For related syntheses of α,β-unsaturated aldehydes based on the palladium-catalyzed reaction of aryl halides with a three carbon partner, see: (a) Patel, B. A.; Kim, J.-I.; Bender, D. D.; Kao, L.-C.; Heck, R. F. J. Org. Chem. 1981, 46, 1061. (b) Jeffery, T. J. J. Chem. Soc., Chem. Commun. 1984, 1287. (c) Unroe, M. R.; Reinhardt, B. A. Synthesis 1987, 981. (d) Parrain, J.-L.; Duchene, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187. (e) Phuan, P.-W.; Kozlowski, M. C. Tetrahedron Lett. 2001, 42, 3963.
5. For related syntheses of α,β-unsaturated aldehydes based on the palladium-catalyzed reaction of aryl halides with a three carbon partner, see: (a) Patel, B. A.; Kim, J.-I.; Bender, D. D.; Kao, L.-C.; Heck, R. F. J. Org. Chem. 1981, 46, 1061. (b) Jeffery, T. J. J. Chem. Soc., Chem. Commun. 1984, 1287. (c) Unroe, M. R.; Reinhardt, B. A. Synthesis 1987, 981. (d) Parrain, J.-L.; Duchene, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187. (e) Phuan, P.-W.; Kozlowski, M. C. Tetrahedron Lett. 2001, 42, 3963.
6. For related syntheses of α,β-unsaturated aldehydes based on the palladium-catalyzed reaction of aryl halides with a three carbon partner, see: (a) Patel, B. A.; Kim, J.-I.; Bender, D. D.; Kao, L.-C.; Heck, R. F. J. Org. Chem. 1981, 46, 1061. (b) Jeffery, T. J. J. Chem. Soc., Chem. Commun. 1984, 1287. (c) Unroe, M. R.; Reinhardt, B. A. Synthesis 1987, 981. (d) Parrain, J.-L.; Duchene, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187. (e) Phuan, P.-W.; Kozlowski, M. C. Tetrahedron Lett. 2001, 42, 3963.
7. For related syntheses of α,β-unsaturated aldehydes based on the palladium-catalyzed reaction of aryl halides with a three carbon partner, see: (a) Patel, B. A.; Kim, J.-I.; Bender, D. D.; Kao, L.-C.; Heck, R. F. J. Org. Chem. 1981, 46, 1061. (b) Jeffery, T. J. J. Chem. Soc., Chem. Commun. 1984, 1287. (c) Unroe, M. R.; Reinhardt, B. A. Synthesis 1987, 981. (d) Parrain, J.-L.; Duchene, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187. (e) Phuan, P.-W.; Kozlowski, M. C. Tetrahedron Lett. 2001, 42, 3963.
8. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
9. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
10. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
11. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
12. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
13. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
14. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
15. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
16. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
17. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
18. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
19. For some recent references, see for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217. (b) Shiina, I.; Imai, Y.; Suzuki, M.; Yanagisawa, M.; Mukaiyama, T. Chem. Lett. 2000, 1062. (c) Svensson, A.; Fex, T.; Kihlberg, J. J. Comb. Chem. 2000, 2, 736. (d) Takeda, T.; Takagi, Y.; Saeki, N.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 8377. (e) Fakhri, S. A.; Yousefi, B. H. Tetrahedron 2000, 56, 8301. (f) Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 2000, 41, 2515. (g) Bulman, P.; Philip, C.; McKenzie, M. J.; Allin, S. M.; Buckle, D. R. Tetrahedron 2000, 56, 9683. (h) Yang, D.; Wong, M.-K.; Yan, Z. J. Org. Chem. 2000, 65, 4179. (i) Rahim, Md. A.; Sasaki, H.; Saito, J.; Fujiwara, T.; Takeda, T. Chem. Commun. 2001, 625. (j) Hess, S.; Dolker, M.; Haferburg, D.; Kertscher, H. P.; Matysik, F.-M.; Ortwein, J.; Teubert, U.; Zimmermann, W.; Eger, K. Pharmazie 2001, 56, 306. (k) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (l) Matsubara, K.; Iura, T.; Maki, T.; Nagashima, H. J. Org. Chem. 2002, 67, 4985.
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28. 4: C, 70.65; H, 6.37; N, 5.90. Found: C, 70.61; H, 6.34; N, 5.95.
29. 2, omitting treatment with HCl.
30. 4: C, 69.04; H, 7.97. Found: C, 69.09; H, 7.93.
31. For palladium-catalyzed coupling of aryl halides, see for example: (a) Organozinc compounds: Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955. (b) See also: Nakamura, E.; Aoki, S.; Sekyia, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (c) 1-Tributylstannyl-3,3-diethoxyprop-1-ene: Parrain, J.-L.; Duchene, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187. (d) Alkyltrifluorosilanes: Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507.
32. For palladium-catalyzed coupling of aryl halides, see for example: (a) Organozinc compounds: Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955. (b) See also: Nakamura, E.; Aoki, S.; Sekyia, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (c) 1-Tributylstannyl-3,3-diethoxyprop-1-ene: Parrain, J.-L.; Duchene, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187. (d) Alkyltrifluorosilanes: Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507.
33. For palladium-catalyzed coupling of aryl halides, see for example: (a) Organozinc compounds: Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955. (b) See also: Nakamura, E.; Aoki, S.; Sekyia, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (c) 1-Tributylstannyl-3,3-diethoxyprop-1-ene: Parrain, J.-L.; Duchene, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187. (d) Alkyltrifluorosilanes: Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507.
34. For palladium-catalyzed coupling of aryl halides, see for example: (a) Organozinc compounds: Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955. (b) See also: Nakamura, E.; Aoki, S.; Sekyia, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (c) 1-Tributylstannyl-3,3-diethoxyprop-1-ene: Parrain, J.-L.; Duchene, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187. (d) Alkyltrifluorosilanes: Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507.
35. For nickel-catalyzed coupling of alkyl iodides, see for example: Arylzinc compounds: Giovannini, R.; Knochel, P. J. Am. Chem. Soc. 1998, 120, 11186.
36. For the nickel-catalyzed reaction of organic halides with olefins in the presence of zinc, see for example: Sustmann, R.; Hopp, P.; Holl, P. Tetrahedron Lett. 1989, 30, 689.
37. For electrochemical methods involving aryl halides and transition metal catalysis, see for example: (a) Condon-Gueugnot, S.; Léonel, E.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1995, 60, 7684. (b) Kurono, N.; Sugita, K.; Takasugi, S.; Tokuda, M. Tetrahedron 1999, 55, 6097. (c) Gomes, P.; Gosmini, C.; Nédélec, J.-Y.; Périchon, J. Tetrahedron Lett. 2002, 43, 5901.
38. For electrochemical methods involving aryl halides and transition metal catalysis, see for example: (a) Condon-Gueugnot, S.; Léonel, E.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1995, 60, 7684. (b) Kurono, N.; Sugita, K.; Takasugi, S.; Tokuda, M. Tetrahedron 1999, 55, 6097. (c) Gomes, P.; Gosmini, C.; Nédélec, J.-Y.; Périchon, J. Tetrahedron Lett. 2002, 43, 5901.
39. For electrochemical methods involving aryl halides and transition metal catalysis, see for example: (a) Condon-Gueugnot, S.; Léonel, E.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1995, 60, 7684. (b) Kurono, N.; Sugita, K.; Takasugi, S.; Tokuda, M. Tetrahedron 1999, 55, 6097. (c) Gomes, P.; Gosmini, C.; Nédélec, J.-Y.; Périchon, J. Tetrahedron Lett. 2002, 43, 5901.
40. For recent references on the synthesis of 3-aryl propanoate esters via reduction of cinnamate esters, see: (a) Taylor, R. A.; Santora, B. P.; Gagne, M. R. Org. Lett. 2000, 2, 1781. (b) Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396. (c) Couturier, M.; Andresen, B. M.; Tucker, J. L.; Dube, P.; Brenek, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2763. (d) Vinson, S. L.; Gagne, M. R. Chem. Commun. 2001, 1130. (e) Desai, B.; Danks, T. N. Tetrahedron Lett. 2001, 42, 5963. (f) Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690. (g) Concellon, J. M.; Rodriguez-Solla, H. Chem.-Eur. J. 2001, 7, 4266. (h) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319. (i) Bremeyer, N. B.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843.
41. For recent references on the synthesis of 3-aryl propanoate esters via reduction of cinnamate esters, see: (a) Taylor, R. A.; Santora, B. P.; Gagne, M. R. Org. Lett. 2000, 2, 1781. (b) Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396. (c) Couturier, M.; Andresen, B. M.; Tucker, J. L.; Dube, P.; Brenek, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2763. (d) Vinson, S. L.; Gagne, M. R. Chem. Commun. 2001, 1130. (e) Desai, B.; Danks, T. N. Tetrahedron Lett. 2001, 42, 5963. (f) Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690. (g) Concellon, J. M.; Rodriguez-Solla, H. Chem.-Eur. J. 2001, 7, 4266. (h) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319. (i) Bremeyer, N. B.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843.
42. For recent references on the synthesis of 3-aryl propanoate esters via reduction of cinnamate esters, see: (a) Taylor, R. A.; Santora, B. P.; Gagne, M. R. Org. Lett. 2000, 2, 1781. (b) Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396. (c) Couturier, M.; Andresen, B. M.; Tucker, J. L.; Dube, P.; Brenek, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2763. (d) Vinson, S. L.; Gagne, M. R. Chem. Commun. 2001, 1130. (e) Desai, B.; Danks, T. N. Tetrahedron Lett. 2001, 42, 5963. (f) Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690. (g) Concellon, J. M.; Rodriguez-Solla, H. Chem.-Eur. J. 2001, 7, 4266. (h) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319. (i) Bremeyer, N. B.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843.
43. For recent references on the synthesis of 3-aryl propanoate esters via reduction of cinnamate esters, see: (a) Taylor, R. A.; Santora, B. P.; Gagne, M. R. Org. Lett. 2000, 2, 1781. (b) Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396. (c) Couturier, M.; Andresen, B. M.; Tucker, J. L.; Dube, P.; Brenek, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2763. (d) Vinson, S. L.; Gagne, M. R. Chem. Commun. 2001, 1130. (e) Desai, B.; Danks, T. N. Tetrahedron Lett. 2001, 42, 5963. (f) Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690. (g) Concellon, J. M.; Rodriguez-Solla, H. Chem.-Eur. J. 2001, 7, 4266. (h) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319. (i) Bremeyer, N. B.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843.
44. For recent references on the synthesis of 3-aryl propanoate esters via reduction of cinnamate esters, see: (a) Taylor, R. A.; Santora, B. P.; Gagne, M. R. Org. Lett. 2000, 2, 1781. (b) Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396. (c) Couturier, M.; Andresen, B. M.; Tucker, J. L.; Dube, P.; Brenek, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2763. (d) Vinson, S. L.; Gagne, M. R. Chem. Commun. 2001, 1130. (e) Desai, B.; Danks, T. N. Tetrahedron Lett. 2001, 42, 5963. (f) Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690. (g) Concellon, J. M.; Rodriguez-Solla, H. Chem.-Eur. J. 2001, 7, 4266. (h) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319. (i) Bremeyer, N. B.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843.
45. For recent references on the synthesis of 3-aryl propanoate esters via reduction of cinnamate esters, see: (a) Taylor, R. A.; Santora, B. P.; Gagne, M. R. Org. Lett. 2000, 2, 1781. (b) Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396. (c) Couturier, M.; Andresen, B. M.; Tucker, J. L.; Dube, P.; Brenek, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2763. (d) Vinson, S. L.; Gagne, M. R. Chem. Commun. 2001, 1130. (e) Desai, B.; Danks, T. N. Tetrahedron Lett. 2001, 42, 5963. (f) Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690. (g) Concellon, J. M.; Rodriguez-Solla, H. Chem.-Eur. J. 2001, 7, 4266. (h) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319. (i) Bremeyer, N. B.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843.
46. For recent references on the synthesis of 3-aryl propanoate esters via reduction of cinnamate esters, see: (a) Taylor, R. A.; Santora, B. P.; Gagne, M. R. Org. Lett. 2000, 2, 1781. (b) Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396. (c) Couturier, M.; Andresen, B. M.; Tucker, J. L.; Dube, P.; Brenek, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2763. (d) Vinson, S. L.; Gagne, M. R. Chem. Commun. 2001, 1130. (e) Desai, B.; Danks, T. N. Tetrahedron Lett. 2001, 42, 5963. (f) Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690. (g) Concellon, J. M.; Rodriguez-Solla, H. Chem.-Eur. J. 2001, 7, 4266. (h) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319. (i) Bremeyer, N. B.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843.
47. For recent references on the synthesis of 3-aryl propanoate esters via reduction of cinnamate esters, see: (a) Taylor, R. A.; Santora, B. P.; Gagne, M. R. Org. Lett. 2000, 2, 1781. (b) Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396. (c) Couturier, M.; Andresen, B. M.; Tucker, J. L.; Dube, P.; Brenek, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2763. (d) Vinson, S. L.; Gagne, M. R. Chem. Commun. 2001, 1130. (e) Desai, B.; Danks, T. N. Tetrahedron Lett. 2001, 42, 5963. (f) Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690. (g) Concellon, J. M.; Rodriguez-Solla, H. Chem.-Eur. J. 2001, 7, 4266. (h) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319. (i) Bremeyer, N. B.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843.
48. For recent references on the synthesis of 3-aryl propanoate esters via reduction of cinnamate esters, see: (a) Taylor, R. A.; Santora, B. P.; Gagne, M. R. Org. Lett. 2000, 2, 1781. (b) Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396. (c) Couturier, M.; Andresen, B. M.; Tucker, J. L.; Dube, P.; Brenek, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2763. (d) Vinson, S. L.; Gagne, M. R. Chem. Commun. 2001, 1130. (e) Desai, B.; Danks, T. N. Tetrahedron Lett. 2001, 42, 5963. (f) Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690. (g) Concellon, J. M.; Rodriguez-Solla, H. Chem.-Eur. J. 2001, 7, 4266. (h) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319. (i) Bremeyer, N. B.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843.