A New Palladium-Catalyzed Intramolecular Allylation to Pyrrolidin-2-ones

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 804-807

  Giambastiani, Giuliano ^a   Pacini, Barbara ^a   Porcelloni, Marina ^a   Poli, Giovanni ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

6 [[1 (3,4 DIHYDRO 8 HYDROXY 1 OXO 1H 2 BENZOPYRAN 3 YL) 3 METHYLBUTYL]AMINO] 4,5 DIHYDROXY 6 OXO 3 AMMONIOHEXANOATE; BACLOFEN; GAMMA LACTAM DERIVATIVE; PALLADIUM; PYRROLIDINE DERIVATIVE;

ALKYLATION; ARTICLE; BINDING AFFINITY; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032489025     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971849+     Document Type: Article

References (59)

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26. For excellent reviews see: (a) Hegedus, L. Palladium in Organic Chemistry. In Organometallics in Synthesis; Schlösser, M., Ed.; J. Wiley: New York, 1994; Chapter 5, pp 385-459. (b) Palladium Reagents and Catalysis, Tsuji, J.; Ed.; Wiley: New York, 1995.
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29. Reviews: (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173; (b) Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975. See also (c) Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113.
30. Reviews: (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173; (b) Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975. See also (c) Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113.
31. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
32. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
33. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
34. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
35. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
36. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
37. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
38. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
39. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
40. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
41. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
42. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
43. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
44. Intramolecular ring closures to pyrrolidine derivatives via π-allyl palladium complexes. Allylic aminations: (a) Trost, B. M.; Genêt, J. P. J. Am. Chem. Soc. 1976, 98, 8516. (b) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247. (c) Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927. (d) Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821. (e) Bäckvall, J. E. Andersson, P. J. Am. Chem. Soc. 1990, 112, 3683. (f) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482. (g) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. Metallo-ene reactions: (i) Oppolzer, W.; Birkinshaw, T. M.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Pyrrolidones via allylic amidations: (j) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157. (k) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016. For an example of ring closure via chloropalladation see: (1) Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945. For two examples of palladium-catalyzed amide anion intramolecular via allylic alkylation see: (m) Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1986, 51, 486. (n) Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J. Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
45. For a related approach using radical chemistry see: Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573.
46. Tsuji, J.; Kobayashi, Y.; Kataoka, H.; Takahashi, T. Tetrahedron Lett. 1980, 21, 1475.
47. Nystrom, J. E.; Rein, T.; Bäckvall, J. E. Org. Synth. 1988, 67, 105
48. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143.
49. Trost, B. M. Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730.
50. 1H-NMR spectrum.
51. Since in the isomerization of (Z)-2 to (E)-2 (Table 1, entry 5), where a potentially enolizing base is absent and 3 was again obtained in trans stereochemistry, we favor the first hypothesis.
52. (a) Mori, M.; Kanda, N.; Oda, I.; Ban, Y. Tetrahedron 1985, 41, 5474.
53. (b) Mori, M.; Kubo, Y.; Ban, Y. Tetrahedron Lett. 1985, 26, 1519.
54. (a) Tsuji, J.; Yamakawa, T.; Kaito, M.; Mandai, T. Tetrahedron Lett. 1978, 19, 2075.
55. (b) Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron Lett. 1979, 20, 2301.
56. (c) Trost, B. M.; Fortunak, J. M. J. Am. Chem. Soc. 1980, 102, 2841.
57. (d) Yamamoto, K., Suzuki, S.; Tsuji, J. Bull. Chem. Soc. Jpn. 1981, 54, 2541.
58. (e) Trost, B. M.; Fortunak, J. M. Tetrahedron Lett. 1981, 22, 2301.
59. (f) See also: Takacs, J. M.; Lawson, E. C.; Clement, F. 213th ACS National Meeting, San Francisco, 1997, abstract 633.