Enantioselective alkynylation of ketones catalyzed by Zn(salen) complexes

Angewandte Chemie - International Edition

Volumn 42, Issue 25, 2003, Pages 2895-2898

  Cozzi, Pier Giorgio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Alkynes; Asymmetric catalysis; Ketones; Salen; Tertiary alcohols

Indexed keywords

CATALYSIS; COMPLEXATION; STEREOCHEMISTRY; ZINC;

ALKYNYLATION;

KETONES;

KETONE DERIVATIVE; ZINC COMPLEX;

ADDITION REACTION; ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038711344     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351230     Document Type: Article

References (47)

1. J. Mulzer in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, pp. 35-97.
2. 2Zn: b) D. J. Ramón, M. Yus, Tetrahedron 1998, 54, 5651-5666; c) C. Garcia, L. K. LaRochelle, P. J. Walsh, J. Am. Chem. Soc. 2002, 124, 10970-10971; d) E. F. DiMauro, M. C. Kozlowski, J. Am. Chem. Soc. 2002, 124, 12668-12669.
3. 2Zn: b) D. J. Ramón, M. Yus, Tetrahedron 1998, 54, 5651-5666; c) C. Garcia, L. K. LaRochelle, P. J. Walsh, J. Am. Chem. Soc. 2002, 124, 10970-10971; d) E. F. DiMauro, M. C. Kozlowski, J. Am. Chem. Soc. 2002, 124, 12668-12669.
4. 2Zn: b) D. J. Ramón, M. Yus, Tetrahedron 1998, 54, 5651-5666; c) C. Garcia, L. K. LaRochelle, P. J. Walsh, J. Am. Chem. Soc. 2002, 124, 10970-10971; d) E. F. DiMauro, M. C. Kozlowski, J. Am. Chem. Soc. 2002, 124, 12668-12669.
5. 2Zn: b) D. J. Ramón, M. Yus, Tetrahedron 1998, 54, 5651-5666; c) C. Garcia, L. K. LaRochelle, P. J. Walsh, J. Am. Chem. Soc. 2002, 124, 10970-10971; d) E. F. DiMauro, M. C. Kozlowski, J. Am. Chem. Soc. 2002, 124, 12668-12669.
6. a) S. Casolari, D. D'Addario, E. Tagliavini, Org. Lett. 1999, 1, 1061-1063;
7. b) H. Hanawa, S. Kii, K. Maruoka, Adv. Synth. Catal. 2001, 343, 57-60;
8. c) A. Cunningham, S. Woodward, Synlett 2002, 43-44;
9. K. M. Waltz, J. Gavenonis, P. J. Walsh, Angew. Chem. 2002, 114, 3849-3852; Angew. Chem. Int. Ed. 2002, 41, 3697-3699.
10. K. M. Waltz, J. Gavenonis, P. J. Walsh, Angew. Chem. 2002, 114, 3849-3852; Angew. Chem. Int. Ed. 2002, 41, 3697-3699.
11. For a recent review, see: G. J. Rowlands, Tetrahedron 2001, 57, 1865-1882.
12. H. Deng, M. P. Isler, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2002, 114, 1051-1054; Angew. Chem. Int. Ed. 2002, 41, 1009-1012.
13. H. Deng, M. P. Isler, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2002, 114, 1051-1054; Angew. Chem. Int. Ed. 2002, 41, 1009-1012.
14. Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412-7413.
15. a) K. B. Hansen, J. L. Leighton, N. E. Jacobsen, J. Am. Chem. Soc. 1996, 118, 10924-10925;
16. b) R. G. Konsler, J. Karl, N. E. Jacobsen, J. Am. Chem. Soc. 1998, 120, 10780-10781;
17. c) D. A. Annis, N. E. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147-4154;
18. d) J. M. Ready, N. E. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688;
19. e) Y. N. Belokon', S. Caveda-Cepas, B. Green, N. S. Ikonnikov, V. N. Krustalev, V. S. Larichev, M. A. Moscalenko, M. North, L. Orizu, V. I. Tararov, M. Tasinazzo, G. I. Timofeeva, V. Yashkina, J. Am. Chem. Soc. 1999, 121, 3968-3973.
20. a) P. G. Cozzi, A. Papa, A. Umani-Ronchi, Tetrahedron Lett. 1996, 37, 4613-4616;
21. b) E. DiMauro, M. Kozlowski, Org. Lett. 2002, 4, 3781-3784.
22. For the highly enantioselective alkynylation of a ketone used in the synthesis of efavirenz, see: L. Tan, C. Chen, R. D. Tillyer, E. J. J. Grabowski, P. J. Reider, Angew. Chem. 1999, 111, 724-727; Angew. Chem. Int. Ed. 1999, 38, 711-713.
23. For the highly enantioselective alkynylation of a ketone used in the synthesis of efavirenz, see: L. Tan, C. Chen, R. D. Tillyer, E. J. J. Grabowski, P. J. Reider, Angew. Chem. 1999, 111, 724-727; Angew. Chem. Int. Ed. 1999, 38, 711-713.
24. a) D. E. Frantz, R. Fässler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806-1807;
25. b) D. Boyall, F. López, H. Sasaki, D. E. Frantz, E. M. Carreira, Org. Lett. 2000, 2, 4233-4236;
26. c) D. E. Frantz, R Fässler, C. S. Tomooka, E. M. Carreira, Acc. Chem. Res. 2000, 33, 373-381;
27. d) J. W. Bode, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, 3611-3612;
28. e) N. K. Anad, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, 9687-9688.
29. B. Jiang, Z. Chen, X. Tang, Org. Lett. 2002, 4, 3451-3453.
30. a) G. Lu, X. Li, W. L. Chan, A. S. C. Chan, Chem. Commun. 2002, 172-173;
31. b) X. Li, G. Lu, W. H. Kwok, A. S. C. Chan, J. Am. Chem. Soc. 2002, 124, 12636-12637;
32. c) G. Gao, D. Moore, R.-G. Xie, L. Pu, Org. Lett. 2002, 4, 4143-4146;
33. d) M.-H. Xu, L. Pu, Org. Lett. 2002, 4, 4555-4557.
34. a) G. A. Morris, H. Zhou, C. L. Stern, S. T. Nguyen, Inorg. Chem. 2001, 40, 3222-3227;
35. b) E. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 3053-3056.
36. The direct use of a Zn(salen) complex, preprepared according to reference [13a], afforded the same result in the addition of phenylacetylene to acetophenone.
37. 2Zn to aldehydes with high enantioselectivity; see: a) K. Mikami, R. Angelaud, K. Ding, A. Ishii, A. Tanaka, N. Sawada, K. Kudo, M. Senda, Eur. J. Org. Chem. 2001, 7, 730-737; b) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523; Angew. Chem. Int. Ed. 1999, 38, 497-501; unfortunately this approach was unsuccessful in our case.
38. 2Zn to aldehydes with high enantioselectivity; see: a) K. Mikami, R. Angelaud, K. Ding, A. Ishii, A. Tanaka, N. Sawada, K. Kudo, M. Senda, Eur. J. Org. Chem. 2001, 7, 730-737; b) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523; Angew. Chem. Int. Ed. 1999, 38, 497-501; unfortunately this approach was unsuccessful in our case.
39. 2Zn to aldehydes with high enantioselectivity; see: a) K. Mikami, R. Angelaud, K. Ding, A. Ishii, A. Tanaka, N. Sawada, K. Kudo, M. Senda, Eur. J. Org. Chem. 2001, 7, 730-737; b) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523; Angew. Chem. Int. Ed. 1999, 38, 497-501; unfortunately this approach was unsuccessful in our case.
40. The reaction of chalcone gave a mixture of the 1,2- and the 1,4-adducts.
41. Methyl and phenyl pyruvate reacted smoothly in our catalytic system without by-product formation and the corresponding product was isolated in high yield (85-90%), although unfortunately as a racemic mixture.
42. M. Bertrand, J.-P. Dulcere, G. Gil, Tetrahedron Lett. 1980, 21, 1945-1948.
43. H. B. Kagan, Adv. Synth. Catal. 2001, 343, 227-233.
44. For crystal data on the coordination of metals to the oxygen atoms of Schiff bases of this type, see: a) J. P. Corden, W. Errington, P. Moore, M. G. H. Wallbridge, Chem. Commun. 1999, 323-324; b) E. Gallo, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1997, 36, 2178-2186; c) D. Cunningham, P. McArdle, M. Mitchell, N. Ní Chonchubhair, M. O'Gara, F. Franceschi, C. Floriani, Inorg. Chem. 2000, 39, 1639-1649; d) B. Cashin, D. Cunningham, P. Daly, P. McArdle, M. Munroe, N. Ní Chonchubhair, Inorg. Chem. 2002, 41, 773-782.
45. For crystal data on the coordination of metals to the oxygen atoms of Schiff bases of this type, see: a) J. P. Corden, W. Errington, P. Moore, M. G. H. Wallbridge, Chem. Commun. 1999, 323-324; b) E. Gallo, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1997, 36, 2178-2186; c) D. Cunningham, P. McArdle, M. Mitchell, N. Ní Chonchubhair, M. O'Gara, F. Franceschi, C. Floriani, Inorg. Chem. 2000, 39, 1639-1649; d) B. Cashin, D. Cunningham, P. Daly, P. McArdle, M. Munroe, N. Ní Chonchubhair, Inorg. Chem. 2002, 41, 773-782.
46. For crystal data on the coordination of metals to the oxygen atoms of Schiff bases of this type, see: a) J. P. Corden, W. Errington, P. Moore, M. G. H. Wallbridge, Chem. Commun. 1999, 323-324; b) E. Gallo, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1997, 36, 2178-2186; c) D. Cunningham, P. McArdle, M. Mitchell, N. Ní Chonchubhair, M. O'Gara, F. Franceschi, C. Floriani, Inorg. Chem. 2000, 39, 1639-1649; d) B. Cashin, D. Cunningham, P. Daly, P. McArdle, M. Munroe, N. Ní Chonchubhair, Inorg. Chem. 2002, 41, 773-782.
47. For crystal data on the coordination of metals to the oxygen atoms of Schiff bases of this type, see: a) J. P. Corden, W. Errington, P. Moore, M. G. H. Wallbridge, Chem. Commun. 1999, 323-324; b) E. Gallo, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1997, 36, 2178-2186; c) D. Cunningham, P. McArdle, M. Mitchell, N. Ní Chonchubhair, M. O'Gara, F. Franceschi, C. Floriani, Inorg. Chem. 2000, 39, 1639-1649; d) B. Cashin, D. Cunningham, P. Daly, P. McArdle, M. Munroe, N. Ní Chonchubhair, Inorg. Chem. 2002, 41, 773-782.