Three-component reaction of aryl diazoacetates, alcohols, and aldehydes (or imines): Evidence of alcoholic oxonium ylide intermediates

Organic Letters

Volumn 7, Issue 1, 2005, Pages 83-86

  Lu, Chong Dao ^a   Liu, Hui ^a   Chen, Zhi Yong ^a   Hu, Wen Hao ^a   Mi, Ai Qiao ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; CARBON; HYDROGEN; IMINE; OXYGEN;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON; HYDROGEN BOND;

EID: 12344276977     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0478483     Document Type: Article

References (39)

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13. For sulfonium ylides, see: (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (h) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (i) Aggarwal, V. K. Synlett 1998, 329. (j) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. (k) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747. (l) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J. Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926. (m) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
14. For sulfonium ylides, see: (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (h) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (i) Aggarwal, V. K. Synlett 1998, 329. (j) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. (k) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747. (l) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J. Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926. (m) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
15. For sulfonium ylides, see: (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (h) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (i) Aggarwal, V. K. Synlett 1998, 329. (j) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. (k) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747. (l) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J. Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926. (m) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
16. For sulfonium ylides, see: (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (h) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (i) Aggarwal, V. K. Synlett 1998, 329. (j) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. (k) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747. (l) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J. Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926. (m) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
17. For sulfonium ylides, see: (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (h) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (i) Aggarwal, V. K. Synlett 1998, 329. (j) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. (k) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747. (l) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J. Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926. (m) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
18. For sulfonium ylides, see: (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (h) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (i) Aggarwal, V. K. Synlett 1998, 329. (j) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. (k) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747. (l) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J. Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926. (m) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
19. For sulfonium ylides, see: (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (h) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (i) Aggarwal, V. K. Synlett 1998, 329. (j) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. (k) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747. (l) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J. Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926. (m) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
20. For sulfonium ylides, see: (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (h) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (i) Aggarwal, V. K. Synlett 1998, 329. (j) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. (k) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747. (l) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J. Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926. (m) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
21. For sulfonium ylides, see: (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (h) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (i) Aggarwal, V. K. Synlett 1998, 329. (j) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. (k) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747. (l) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J. Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926. (m) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
22. Ethereal oxonium ylides. For [1,2] rearrangement, see: (n) Eberlein, T. H.; West, F. G.; Tester, R. W. J. Org. Chem. 1992, 57, 3479. (o) West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892. (p) Marmsater, F. P.; West, F. G.; J. Am. Chem. Soc. 2001, 123, 5144. (q) Marmsater, F. P.; Vanecko, J. A. West, F. G. Tetrahedron 2002, 58, 2027. (r) Marmsater, F. P.; Murphy, G. K.; West, F. G. J. Am. Chem. Soc. 2003, 125, 14724.
23. Ethereal oxonium ylides. For [1,2] rearrangement, see: (n) Eberlein, T. H.; West, F. G.; Tester, R. W. J. Org. Chem. 1992, 57, 3479. (o) West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892. (p) Marmsater, F. P.; West, F. G.; J. Am. Chem. Soc. 2001, 123, 5144. (q) Marmsater, F. P.; Vanecko, J. A. West, F. G. Tetrahedron 2002, 58, 2027. (r) Marmsater, F. P.; Murphy, G. K.; West, F. G. J. Am. Chem. Soc. 2003, 125, 14724.
24. Ethereal oxonium ylides. For [1,2] rearrangement, see: (n) Eberlein, T. H.; West, F. G.; Tester, R. W. J. Org. Chem. 1992, 57, 3479. (o) West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892. (p) Marmsater, F. P.; West, F. G.; J. Am. Chem. Soc. 2001, 123, 5144. (q) Marmsater, F. P.; Vanecko, J. A. West, F. G. Tetrahedron 2002, 58, 2027. (r) Marmsater, F. P.; Murphy, G. K.; West, F. G. J. Am. Chem. Soc. 2003, 125, 14724.
25. Ethereal oxonium ylides. For [1,2] rearrangement, see: (n) Eberlein, T. H.; West, F. G.; Tester, R. W. J. Org. Chem. 1992, 57, 3479. (o) West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892. (p) Marmsater, F. P.; West, F. G.; J. Am. Chem. Soc. 2001, 123, 5144. (q) Marmsater, F. P.; Vanecko, J. A. West, F. G. Tetrahedron 2002, 58, 2027. (r) Marmsater, F. P.; Murphy, G. K.; West, F. G. J. Am. Chem. Soc. 2003, 125, 14724.
26. Ethereal oxonium ylides. For [1,2] rearrangement, see: (n) Eberlein, T. H.; West, F. G.; Tester, R. W. J. Org. Chem. 1992, 57, 3479. (o) West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892. (p) Marmsater, F. P.; West, F. G.; J. Am. Chem. Soc. 2001, 123, 5144. (q) Marmsater, F. P.; Vanecko, J. A. West, F. G. Tetrahedron 2002, 58, 2027. (r) Marmsater, F. P.; Murphy, G. K.; West, F. G. J. Am. Chem. Soc. 2003, 125, 14724.
27. For [2,3] rearrangement, see: (s) Clark, J. S. Tetrahedron Lett. 1992, 33, 6193. (t) Clark, J. S.; Dossetter, A. G.; Blake, A. J.; Li, W.-S.; Whittingham, W. G. Chem. Commun. 1999, 749. (u) Clark, J. S.; Bate, A. L.; Grinter, T. Chem. Commun. 2001, 459. (v) Clark, J. S.; Whitlock, G.; Jiang, S.; Onyia, N. Chem. Commun. 2003, 2578. (w) Clark, J. S.; Fessard, T. S.; Wilson, C. Org. Lett. 2004, 6, 1773.
28. For [2,3] rearrangement, see: (s) Clark, J. S. Tetrahedron Lett. 1992, 33, 6193. (t) Clark, J. S.; Dossetter, A. G.; Blake, A. J.; Li, W.-S.; Whittingham, W. G. Chem. Commun. 1999, 749. (u) Clark, J. S.; Bate, A. L.; Grinter, T. Chem. Commun. 2001, 459. (v) Clark, J. S.; Whitlock, G.; Jiang, S.; Onyia, N. Chem. Commun. 2003, 2578. (w) Clark, J. S.; Fessard, T. S.; Wilson, C. Org. Lett. 2004, 6, 1773.
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30. For [2,3] rearrangement, see: (s) Clark, J. S. Tetrahedron Lett. 1992, 33, 6193. (t) Clark, J. S.; Dossetter, A. G.; Blake, A. J.; Li, W.-S.; Whittingham, W. G. Chem. Commun. 1999, 749. (u) Clark, J. S.; Bate, A. L.; Grinter, T. Chem. Commun. 2001, 459. (v) Clark, J. S.; Whitlock, G.; Jiang, S.; Onyia, N. Chem. Commun. 2003, 2578. (w) Clark, J. S.; Fessard, T. S.; Wilson, C. Org. Lett. 2004, 6, 1773.
31. For [2,3] rearrangement, see: (s) Clark, J. S. Tetrahedron Lett. 1992, 33, 6193. (t) Clark, J. S.; Dossetter, A. G.; Blake, A. J.; Li, W.-S.; Whittingham, W. G. Chem. Commun. 1999, 749. (u) Clark, J. S.; Bate, A. L.; Grinter, T. Chem. Commun. 2001, 459. (v) Clark, J. S.; Whitlock, G.; Jiang, S.; Onyia, N. Chem. Commun. 2003, 2578. (w) Clark, J. S.; Fessard, T. S.; Wilson, C. Org. Lett. 2004, 6, 1773.
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37. 4.
38. 4 = dirhodium tetrakis(S-(N-1,8- naphthoyl) tert-leucinate).
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