Palladium(0)-Catalyzed Allylation of Highly Acidic and Nonnucleophilic Anilines. the Origin of Stereochemical Scrambling When Using Allylic Carbonates

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6160-6166

  Moreno Mañas, Marcial ^a   Morral, Lurdes ^a   Pleixats, Roser ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001147749     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980209j     Document Type: Article

References (64)

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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) 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. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (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.
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