Zn-alkynylide additions to acyl iminiums

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1497-1499

  Fischer, Christian ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACID HALIDE; ALKYNE DERIVATIVE; IMINE; IMINIUM DERIVATIVE; PHOSPHINIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE;

EID: 2442564600     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049578u     Document Type: Article

References (65)

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3. For selected examples of the use of optically active propargylic alcohols in synthesis, see: (a) Trost, B. M.; Hipskind, P. A.; Chung, J. Y. L.; Chan, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1502. (b) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1992, 57, 1242. (c) Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457. (d) Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
4. For selected examples of the use of optically active propargylic alcohols in synthesis, see: (a) Trost, B. M.; Hipskind, P. A.; Chung, J. Y. L.; Chan, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1502. (b) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1992, 57, 1242. (c) Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457. (d) Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
5. For selected examples of the use of optically active propargylic alcohols in synthesis, see: (a) Trost, B. M.; Hipskind, P. A.; Chung, J. Y. L.; Chan, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1502. (b) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1992, 57, 1242. (c) Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457. (d) Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
6. Stoichiometric reductions: (a) Midland, M. M.; Tramontano, A.; Zderic, S. A. J. Am. Chem. Soc. 1977, 99, 5211. (b) Yamaguchi, S.; Mosher, H. S.; Pohland, A. J. Am. Chem. Soc. 1972, 94, 9254. (c) Nishizawa, M.; Yamada, M.; Noyori, R. Tetrahedron Lett. 1981, 22, 247. (d) Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16.
7. Stoichiometric reductions: (a) Midland, M. M.; Tramontano, A.; Zderic, S. A. J. Am. Chem. Soc. 1977, 99, 5211. (b) Yamaguchi, S.; Mosher, H. S.; Pohland, A. J. Am. Chem. Soc. 1972, 94, 9254. (c) Nishizawa, M.; Yamada, M.; Noyori, R. Tetrahedron Lett. 1981, 22, 247. (d) Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16.
8. Stoichiometric reductions: (a) Midland, M. M.; Tramontano, A.; Zderic, S. A. J. Am. Chem. Soc. 1977, 99, 5211. (b) Yamaguchi, S.; Mosher, H. S.; Pohland, A. J. Am. Chem. Soc. 1972, 94, 9254. (c) Nishizawa, M.; Yamada, M.; Noyori, R. Tetrahedron Lett. 1981, 22, 247. (d) Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16.
9. Stoichiometric reductions: (a) Midland, M. M.; Tramontano, A.; Zderic, S. A. J. Am. Chem. Soc. 1977, 99, 5211. (b) Yamaguchi, S.; Mosher, H. S.; Pohland, A. J. Am. Chem. Soc. 1972, 94, 9254. (c) Nishizawa, M.; Yamada, M.; Noyori, R. Tetrahedron Lett. 1981, 22, 247. (d) Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16.
10. Catalytic methods: (a) Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938. (b) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
11. Catalytic methods: (a) Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938. (b) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
12. For the addition of lithium and magnesium acetylides to trifluoro-methyl aryl ketones, see: (a) Tan, L.; Chen, C.-Y.; Tillyer, R. D.; Grabowski, E. J. J.; Reider, P. Angew. Chem., Int. Ed. 1999, 38, 711. (b) For a recent report on the addition of aromatic aldehydes with alkynylzinc reagents generated in situ from terminal acetylenes and dimethylzinc, see; Li, Z.; Upadhyay, V.; DeCamp, A. E.; DiMichele, L.; Reider, P. J. Synthesis 1999, 1453. (c) For a recent study of chelation-controlled stannylacetylene additions to aldehydes, see: Evans, D. A.; Halstead, D. P.; Allison, B. D. Tetrahedron Lett. 1999, 40, 4461.
13. For the addition of lithium and magnesium acetylides to trifluoro-methyl aryl ketones, see: (a) Tan, L.; Chen, C.-Y.; Tillyer, R. D.; Grabowski, E. J. J.; Reider, P. Angew. Chem., Int. Ed. 1999, 38, 711. (b) For a recent report on the addition of aromatic aldehydes with alkynylzinc reagents generated in situ from terminal acetylenes and dimethylzinc, see; Li, Z.; Upadhyay, V.; DeCamp, A. E.; DiMichele, L.; Reider, P. J. Synthesis 1999, 1453. (c) For a recent study of chelation-controlled stannylacetylene additions to aldehydes, see: Evans, D. A.; Halstead, D. P.; Allison, B. D. Tetrahedron Lett. 1999, 40, 4461.
14. For the addition of lithium and magnesium acetylides to trifluoro-methyl aryl ketones, see: (a) Tan, L.; Chen, C.-Y.; Tillyer, R. D.; Grabowski, E. J. J.; Reider, P. Angew. Chem., Int. Ed. 1999, 38, 711. (b) For a recent report on the addition of aromatic aldehydes with alkynylzinc reagents generated in situ from terminal acetylenes and dimethylzinc, see; Li, Z.; Upadhyay, V.; DeCamp, A. E.; DiMichele, L.; Reider, P. J. Synthesis 1999, 1453. (c) For a recent study of chelation-controlled stannylacetylene additions to aldehydes, see: Evans, D. A.; Halstead, D. P.; Allison, B. D. Tetrahedron Lett. 1999, 40, 4461.
15. For addition of alkynilides to imines, see: (a) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. (b) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051. (c) Brasseur, D.; Marek, I.; Normant, J.-F. Tetrahedron 1996, 52, 7235. (d) Sato, Y.; Nishimata, T.; Mori, M. Heterocydes 1997, 44, 443. (e) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J.-L.; Dessinges, A. Synlett 1998, 3, 251. (f) Courtois, G.; Desre, V.; Miginiac, L. J. Organomet. Chem. 1998, 570, 279. (g) Florio, S.; Troisi, L.; Capriati, V.; Suppa, G. Eur. J. Org. Chem. 2000, 65, 3793. (h) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
16. For addition of alkynilides to imines, see: (a) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. (b) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051. (c) Brasseur, D.; Marek, I.; Normant, J.-F. Tetrahedron 1996, 52, 7235. (d) Sato, Y.; Nishimata, T.; Mori, M. Heterocydes 1997, 44, 443. (e) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J.-L.; Dessinges, A. Synlett 1998, 3, 251. (f) Courtois, G.; Desre, V.; Miginiac, L. J. Organomet. Chem. 1998, 570, 279. (g) Florio, S.; Troisi, L.; Capriati, V.; Suppa, G. Eur. J. Org. Chem. 2000, 65, 3793. (h) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
17. For addition of alkynilides to imines, see: (a) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. (b) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051. (c) Brasseur, D.; Marek, I.; Normant, J.-F. Tetrahedron 1996, 52, 7235. (d) Sato, Y.; Nishimata, T.; Mori, M. Heterocydes 1997, 44, 443. (e) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J.-L.; Dessinges, A. Synlett 1998, 3, 251. (f) Courtois, G.; Desre, V.; Miginiac, L. J. Organomet. Chem. 1998, 570, 279. (g) Florio, S.; Troisi, L.; Capriati, V.; Suppa, G. Eur. J. Org. Chem. 2000, 65, 3793. (h) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
18. For addition of alkynilides to imines, see: (a) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. (b) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051. (c) Brasseur, D.; Marek, I.; Normant, J.-F. Tetrahedron 1996, 52, 7235. (d) Sato, Y.; Nishimata, T.; Mori, M. Heterocydes 1997, 44, 443. (e) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J.-L.; Dessinges, A. Synlett 1998, 3, 251. (f) Courtois, G.; Desre, V.; Miginiac, L. J. Organomet. Chem. 1998, 570, 279. (g) Florio, S.; Troisi, L.; Capriati, V.; Suppa, G. Eur. J. Org. Chem. 2000, 65, 3793. (h) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
19. For addition of alkynilides to imines, see: (a) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. (b) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051. (c) Brasseur, D.; Marek, I.; Normant, J.-F. Tetrahedron 1996, 52, 7235. (d) Sato, Y.; Nishimata, T.; Mori, M. Heterocydes 1997, 44, 443. (e) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J.-L.; Dessinges, A. Synlett 1998, 3, 251. (f) Courtois, G.; Desre, V.; Miginiac, L. J. Organomet. Chem. 1998, 570, 279. (g) Florio, S.; Troisi, L.; Capriati, V.; Suppa, G. Eur. J. Org. Chem. 2000, 65, 3793. (h) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
20. For addition of alkynilides to imines, see: (a) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. (b) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051. (c) Brasseur, D.; Marek, I.; Normant, J.-F. Tetrahedron 1996, 52, 7235. (d) Sato, Y.; Nishimata, T.; Mori, M. Heterocydes 1997, 44, 443. (e) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J.-L.; Dessinges, A. Synlett 1998, 3, 251. (f) Courtois, G.; Desre, V.; Miginiac, L. J. Organomet. Chem. 1998, 570, 279. (g) Florio, S.; Troisi, L.; Capriati, V.; Suppa, G. Eur. J. Org. Chem. 2000, 65, 3793. (h) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
21. For addition of alkynilides to imines, see: (a) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. (b) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051. (c) Brasseur, D.; Marek, I.; Normant, J.-F. Tetrahedron 1996, 52, 7235. (d) Sato, Y.; Nishimata, T.; Mori, M. Heterocydes 1997, 44, 443. (e) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J.-L.; Dessinges, A. Synlett 1998, 3, 251. (f) Courtois, G.; Desre, V.; Miginiac, L. J. Organomet. Chem. 1998, 570, 279. (g) Florio, S.; Troisi, L.; Capriati, V.; Suppa, G. Eur. J. Org. Chem. 2000, 65, 3793. (h) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
22. For addition of alkynilides to imines, see: (a) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. (b) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051. (c) Brasseur, D.; Marek, I.; Normant, J.-F. Tetrahedron 1996, 52, 7235. (d) Sato, Y.; Nishimata, T.; Mori, M. Heterocydes 1997, 44, 443. (e) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J.-L.; Dessinges, A. Synlett 1998, 3, 251. (f) Courtois, G.; Desre, V.; Miginiac, L. J. Organomet. Chem. 1998, 570, 279. (g) Florio, S.; Troisi, L.; Capriati, V.; Suppa, G. Eur. J. Org. Chem. 2000, 65, 3793. (h) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
23. For Cu-mediated addition of acetylene gas to N-alkyl imines at elevated temperatures, see: Rohm + Haas Co. U.S. Patent 2 665 311, 1950.
24. For representative additions of other carbanions to imines, see: (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (b) Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 127, 268. (c) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 122, 7138. (d) Knudsen, K.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgensen, K. A. J. Am. Chem. Soc. 2001, 123, 5843. (e) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 984.
25. For representative additions of other carbanions to imines, see: (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (b) Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 127, 268. (c) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 122, 7138. (d) Knudsen, K.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgensen, K. A. J. Am. Chem. Soc. 2001, 123, 5843. (e) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 984.
26. For representative additions of other carbanions to imines, see: (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (b) Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 127, 268. (c) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 122, 7138. (d) Knudsen, K.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgensen, K. A. J. Am. Chem. Soc. 2001, 123, 5843. (e) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 984.
27. For representative additions of other carbanions to imines, see: (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (b) Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 127, 268. (c) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 122, 7138. (d) Knudsen, K.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgensen, K. A. J. Am. Chem. Soc. 2001, 123, 5843. (e) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 984.
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50. Use of acylating reagents to facilitate nucleophilic additions to imines is most commonly employed in additions to heteroaromatic compounds such as quinolines. For selected examples, see: (a) Mori, S.; Iwakura, H.; Takechi, S. Tetrahedron Lett. 1988, 29, 5391. (b) Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem. 1994, 106, 2578. (c) Elbaum, D.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1995, 117, 211. (d) Brana, M. F.; Moran, M.; De Vega, M. J. P.; Pita-Romero, I. J. Org. Chem. 1996, 67, 1369. (e) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A. J. Heterocycl. Chem. 1996, 33, 735. (f) Unno, R.; Michishita, H.; Inagaki, H.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Chem. Pharm. Bull. 1997, 45, 125. (g) Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591. (h) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
51. Use of acylating reagents to facilitate nucleophilic additions to imines is most commonly employed in additions to heteroaromatic compounds such as quinolines. For selected examples, see: (a) Mori, S.; Iwakura, H.; Takechi, S. Tetrahedron Lett. 1988, 29, 5391. (b) Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem. 1994, 106, 2578. (c) Elbaum, D.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1995, 117, 211. (d) Brana, M. F.; Moran, M.; De Vega, M. J. P.; Pita-Romero, I. J. Org. Chem. 1996, 67, 1369. (e) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A. J. Heterocycl. Chem. 1996, 33, 735. (f) Unno, R.; Michishita, H.; Inagaki, H.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Chem. Pharm. Bull. 1997, 45, 125. (g) Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591. (h) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
52. Use of acylating reagents to facilitate nucleophilic additions to imines is most commonly employed in additions to heteroaromatic compounds such as quinolines. For selected examples, see: (a) Mori, S.; Iwakura, H.; Takechi, S. Tetrahedron Lett. 1988, 29, 5391. (b) Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem. 1994, 106, 2578. (c) Elbaum, D.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1995, 117, 211. (d) Brana, M. F.; Moran, M.; De Vega, M. J. P.; Pita-Romero, I. J. Org. Chem. 1996, 67, 1369. (e) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A. J. Heterocycl. Chem. 1996, 33, 735. (f) Unno, R.; Michishita, H.; Inagaki, H.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Chem. Pharm. Bull. 1997, 45, 125. (g) Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591. (h) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
53. Use of acylating reagents to facilitate nucleophilic additions to imines is most commonly employed in additions to heteroaromatic compounds such as quinolines. For selected examples, see: (a) Mori, S.; Iwakura, H.; Takechi, S. Tetrahedron Lett. 1988, 29, 5391. (b) Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem. 1994, 106, 2578. (c) Elbaum, D.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1995, 117, 211. (d) Brana, M. F.; Moran, M.; De Vega, M. J. P.; Pita-Romero, I. J. Org. Chem. 1996, 67, 1369. (e) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A. J. Heterocycl. Chem. 1996, 33, 735. (f) Unno, R.; Michishita, H.; Inagaki, H.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Chem. Pharm. Bull. 1997, 45, 125. (g) Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591. (h) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
54. Use of acylating reagents to facilitate nucleophilic additions to imines is most commonly employed in additions to heteroaromatic compounds such as quinolines. For selected examples, see: (a) Mori, S.; Iwakura, H.; Takechi, S. Tetrahedron Lett. 1988, 29, 5391. (b) Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem. 1994, 106, 2578. (c) Elbaum, D.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1995, 117, 211. (d) Brana, M. F.; Moran, M.; De Vega, M. J. P.; Pita-Romero, I. J. Org. Chem. 1996, 67, 1369. (e) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A. J. Heterocycl. Chem. 1996, 33, 735. (f) Unno, R.; Michishita, H.; Inagaki, H.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Chem. Pharm. Bull. 1997, 45, 125. (g) Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591. (h) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
55. Use of acylating reagents to facilitate nucleophilic additions to imines is most commonly employed in additions to heteroaromatic compounds such as quinolines. For selected examples, see: (a) Mori, S.; Iwakura, H.; Takechi, S. Tetrahedron Lett. 1988, 29, 5391. (b) Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem. 1994, 106, 2578. (c) Elbaum, D.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1995, 117, 211. (d) Brana, M. F.; Moran, M.; De Vega, M. J. P.; Pita-Romero, I. J. Org. Chem. 1996, 67, 1369. (e) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A. J. Heterocycl. Chem. 1996, 33, 735. (f) Unno, R.; Michishita, H.; Inagaki, H.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Chem. Pharm. Bull. 1997, 45, 125. (g) Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591. (h) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
56. Use of acylating reagents to facilitate nucleophilic additions to imines is most commonly employed in additions to heteroaromatic compounds such as quinolines. For selected examples, see: (a) Mori, S.; Iwakura, H.; Takechi, S. Tetrahedron Lett. 1988, 29, 5391. (b) Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem. 1994, 106, 2578. (c) Elbaum, D.; Porco, J. A., Jr.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1995, 117, 211. (d) Brana, M. F.; Moran, M.; De Vega, M. J. P.; Pita-Romero, I. J. Org. Chem. 1996, 67, 1369. (e) Nicolaou, K. C.; Gross, J. L.; Kerr, M. A. J. Heterocycl. Chem. 1996, 33, 735. (f) Unno, R.; Michishita, H.; Inagaki, H.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Chem. Pharm. Bull. 1997, 45, 125. (g) Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591. (h) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
57. We have found that the addition of TMPDA leads to a homogeneous solution of the acetylide in toluene and overall faster, cleaner reactions.
58. For selected recent examples, see: (a) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. (b) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1996, 2631. (c) Gaul, C.; Schaerer, K.; Seebach, D. J. Org. Chem. 2001, 66, 3059. (d) Pinho, P.; Andersson, P. G. Tetrahedron 2001, 57, 1615. (e) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122. (f) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692. (g) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
59. For selected recent examples, see: (a) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. (b) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1996, 2631. (c) Gaul, C.; Schaerer, K.; Seebach, D. J. Org. Chem. 2001, 66, 3059. (d) Pinho, P.; Andersson, P. G. Tetrahedron 2001, 57, 1615. (e) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122. (f) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692. (g) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
60. For selected recent examples, see: (a) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. (b) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1996, 2631. (c) Gaul, C.; Schaerer, K.; Seebach, D. J. Org. Chem. 2001, 66, 3059. (d) Pinho, P.; Andersson, P. G. Tetrahedron 2001, 57, 1615. (e) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122. (f) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692. (g) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
61. For selected recent examples, see: (a) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. (b) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1996, 2631. (c) Gaul, C.; Schaerer, K.; Seebach, D. J. Org. Chem. 2001, 66, 3059. (d) Pinho, P.; Andersson, P. G. Tetrahedron 2001, 57, 1615. (e) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122. (f) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692. (g) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
62. For selected recent examples, see: (a) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. (b) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1996, 2631. (c) Gaul, C.; Schaerer, K.; Seebach, D. J. Org. Chem. 2001, 66, 3059. (d) Pinho, P.; Andersson, P. G. Tetrahedron 2001, 57, 1615. (e) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122. (f) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692. (g) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
63. For selected recent examples, see: (a) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. (b) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1996, 2631. (c) Gaul, C.; Schaerer, K.; Seebach, D. J. Org. Chem. 2001, 66, 3059. (d) Pinho, P.; Andersson, P. G. Tetrahedron 2001, 57, 1615. (e) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122. (f) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692. (g) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
64. For selected recent examples, see: (a) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. (b) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1996, 2631. (c) Gaul, C.; Schaerer, K.; Seebach, D. J. Org. Chem. 2001, 66, 3059. (d) Pinho, P.; Andersson, P. G. Tetrahedron 2001, 57, 1615. (e) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122. (f) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692. (g) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
65. For a recent example, see: Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2003, 125, 761.