Catalytic asymmetric allylation of aldehydes using a chiral silver(I) complex

Journal of the American Chemical Society

Volumn 118, Issue 19, 1996, Pages 4723-4724

  Yanagisawa, Akira ^a   Nakashima, Hiroshi ^a   Ishiba, Atsushi ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX; SILVER DERIVATIVE;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029895814     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9603315     Document Type: Article

References (35)

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2. Allylboranes: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (b) Short, R. P., Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Racherla, U. S.: Brown, H. C. J. Org. Chem. 1991, 56, 401, Allylboronartes. (d) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768. (e) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (f) Roush, W. R.; Walls, A. E., Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (g) Roush, W. R., Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979. (h) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.: Park, J. C. J. Org. Chem. 1990, 55, 4109.
3. Allylboranes: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (b) Short, R. P., Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Racherla, U. S.: Brown, H. C. J. Org. Chem. 1991, 56, 401, Allylboronartes. (d) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768. (e) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (f) Roush, W. R.; Walls, A. E., Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (g) Roush, W. R., Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979. (h) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.: Park, J. C. J. Org. Chem. 1990, 55, 4109.
4. Allylboranes: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (b) Short, R. P., Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Racherla, U. S.: Brown, H. C. J. Org. Chem. 1991, 56, 401, Allylboronartes. (d) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768. (e) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (f) Roush, W. R.; Walls, A. E., Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (g) Roush, W. R., Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979. (h) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.: Park, J. C. J. Org. Chem. 1990, 55, 4109.
5. Allylboranes: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (b) Short, R. P., Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Racherla, U. S.: Brown, H. C. J. Org. Chem. 1991, 56, 401, Allylboronartes. (d) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768. (e) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (f) Roush, W. R.; Walls, A. E., Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (g) Roush, W. R., Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979. (h) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.: Park, J. C. J. Org. Chem. 1990, 55, 4109.
6. Allylboranes: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (b) Short, R. P., Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Racherla, U. S.: Brown, H. C. J. Org. Chem. 1991, 56, 401, Allylboronartes. (d) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768. (e) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (f) Roush, W. R.; Walls, A. E., Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (g) Roush, W. R., Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979. (h) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.: Park, J. C. J. Org. Chem. 1990, 55, 4109.
7. Allylboranes: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (b) Short, R. P., Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Racherla, U. S.: Brown, H. C. J. Org. Chem. 1991, 56, 401, Allylboronartes. (d) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768. (e) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (f) Roush, W. R.; Walls, A. E., Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (g) Roush, W. R., Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979. (h) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.: Park, J. C. J. Org. Chem. 1990, 55, 4109.
8. Allylboranes: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (b) Short, R. P., Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Racherla, U. S.: Brown, H. C. J. Org. Chem. 1991, 56, 401, Allylboronartes. (d) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768. (e) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (f) Roush, W. R.; Walls, A. E., Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (g) Roush, W. R., Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979. (h) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.: Park, J. C. J. Org. Chem. 1990, 55, 4109.
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12. Allyltitanates: (k) Riediker, M.; Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1989, 28, 494. (l) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (m) Hafner, A., Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Sireit, P.: Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321 Allylaluminum derivatives. (n) Minowa, N.; Mukaiyama, T. Bull Chem. Soc Jpn. 1987, 60, 3697.
13. Allyltitanates: (k) Riediker, M.; Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1989, 28, 494. (l) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (m) Hafner, A., Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Sireit, P.: Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321 Allylaluminum derivatives. (n) Minowa, N.; Mukaiyama, T. Bull Chem. Soc Jpn. 1987, 60, 3697.
14. Allyltitanates: (k) Riediker, M.; Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1989, 28, 494. (l) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (m) Hafner, A., Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Sireit, P.: Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321 Allylaluminum derivatives. (n) Minowa, N.; Mukaiyama, T. Bull Chem. Soc Jpn. 1987, 60, 3697.
15. Allylstannanes: (o) Otera, J.; Kawasaki, Y.; Mizuno, H.; Shimizu, Y. Chem. Lett. 1983, 1529 (p) Otera, J.; Yoshinaga, Y.; Yamaji, T.; Yoshioka. T.; Kawasaki, Y. Organometallics 1985, 4, 1213 (q) Boldrini, G P.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun. 1986, 685. (r) Boldrini, G P.; Lodi, L., Tasliavini, E.; Tarasco, C., Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447. (s) Boga, C.; Savoia, D.; Tagliavini, E.; Trombini, C., Umani Ronchi, A. J. Organomet. Chem 1988, 353, 177.
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30. 2.
31. Results of the reaction carried out at various temperatures (temperature, yield, enantioselectivity). 20°C, 16% yield, 79% ee. O°C. 16%-yield, 86% ee: -20°C. 88% yield, 96% ee. -45°C. 54% yield, 94% ee: - 78°C. <1% yield The catalyst was deactivated for prolonged periods above 0°C.
32. 4c
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34. 24 -42.9° (c 6.7. benzene).
35. Although allytributyltin was completely consumed, ca. 50% of benxaldehyde was recovered, probably due to the occurrence of unknown side reactions specific to this stoichiometric reaction system.