Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via π-allylpalladium complex catalyzed by Pd(0)

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9450-9458

  Lee, Kee Young ^a   Kim, Yong Hyun ^a   Park, Min Sung ^a   Oh, Chang Young ^a   Ham, Won Hun ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BENZAMIDE DERIVATIVE; PALLADIUM; PALLADIUM COMPLEX;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLIZATION; ORGANIC CHEMISTRY; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0033601212     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991065r     Document Type: Article

References (109)

1. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
2. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
3. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
4. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
5. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
6. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
7. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
8. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
9. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
10. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
11. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
12. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
13. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
14. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
15. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
16. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (d) Tsuji, J. Tetrahedron 1986, 42, 4361. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (f) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (h) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73. (n) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395. (o) Trost, B. M. Pure Appl. Chem. 1996, 68, 779. (p) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
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