Enantioselective preparation of β,β-disubstituted α-methylenepropionates by MAO promotion of the zinc schlenk equilibrium

Angewandte Chemie - International Edition

Volumn 44, Issue 15, 2005, Pages 2235-2237

  Goldsmith, Paul J ^a   Teat, Simon J ^b   Woodward, Simon ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b DIAMOND LIGHT SOURCE LTD   (United Kingdom)

Author keywords

Allylation; Asymmetric catalysis; Copper zinc

Indexed keywords

BYPRODUCTS; PHASE EQUILIBRIA; ZINC;

CHEMICAL EQUATIONS; ENANTIOSELECTIVITY; METHYLALUMINOXANE (MAO); SCHLENK EQUILIBRIUM;

ORGANIC COMPOUNDS;

EID: 17644390658     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200463028     Document Type: Article

References (30)

1. a) K. Tissot-Croset, D. Polet, A. Alexakis, Angew. Chem. 2004, 116, 2480-2482; Angew. Chem. Int. Ed. 2004, 43, 2426-2428;
2. a) K. Tissot-Croset, D. Polet, A. Alexakis, Angew. Chem. 2004, 116, 2480-2482; Angew. Chem. Int. Ed. 2004, 43, 2426-2428;
3. b) A. O. Larsen, W. Leu, C. N. Oberhuber, J. E. Campbell, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 11130-11131;
4. c) U. Piarulli, P. Daubos, C. Claveric, M. Roux, C. Genari, Angew. Chem. 2003, 115, 244-246; Angew. Chem. Int. Ed. 2003, 42, 234-236;
5. c) U. Piarulli, P. Daubos, C. Claveric, M. Roux, C. Genari, Angew. Chem. 2003, 115, 244-246; Angew. Chem. Int. Ed. 2003, 42, 234-236;
6. d) W.-J. Shi, L.-X. Wang, Y. Fu, S.-F. Zhou, Q.-L. Zhou, Tetrahedron: Asymmetry 2003, 14, 3867-3872;
7. e) H. Malde, A. W. van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171;
8. f) F. Dubner, P. Knochel, Tetrahedron Lett. 2000, 41, 9233-9237.
9. a) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691;
10. b) M. A. Kacrpzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10 676-10 681.
11. N2) has been reported in a patent: P. Knochel, F. Dübner (Avecia Ltd., UK), PCT Int. Appl. WO2000012449, 2000 [Chem. Abstr. 2000, 132, 22 2063].
12. L.-H. Xu, E. P. Kündig, Helv. Chim. Acta 1994, 77, 1480-1484.
13. C Börner, P. J. Goldsmith, S. Woodward, J. Gimeno, S. Gladiali, D. Ramazzotti, Chem. Commun. 2000, 2433-2434.
14. D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
15. D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
16. a) J. Boersma, J. G. Noltes, Tetrahedron Lett. 1966, 1521-1525;
17. -1 < 0.01, see: b) D. F. Evans, I. Wharf, J. Chem. Soc. A 1968, 4, 783-787.
18. The structure of MAO is not known (linear, ring, and cage structures have all been proposed). Structure 4 is given for conceptual purposes only. For lead overviews, see: a) E. Zurek, T. Ziegler, Prog. Polym. Sci. 2004, 29, 107-148; b) P. L. Bryant, C. R. Harwell, A. A. Mrse, E. F. Emery, Z. Gan, T. Caldwell, A. P. Reyes, P. Kuhns, D. W. Hoyt, L. S. Simeral, R. W. Hall, L. G. Butler, J. Am. Chem. Soc. 2001, 123, 12009-12017; c) H. Hanawa, N. Abe, K. Marouka, Tetrahedron Lett. 1999, 40, 5365-5368.
19. The structure of MAO is not known (linear, ring, and cage structures have all been proposed). Structure 4 is given for conceptual purposes only. For lead overviews, see: a) E. Zurek, T. Ziegler, Prog. Polym. Sci. 2004, 29, 107-148; b) P. L. Bryant, C. R. Harwell, A. A. Mrse, E. F. Emery, Z. Gan, T. Caldwell, A. P. Reyes, P. Kuhns, D. W. Hoyt, L. S. Simeral, R. W. Hall, L. G. Butler, J. Am. Chem. Soc. 2001, 123, 12009-12017; c) H. Hanawa, N. Abe, K. Marouka, Tetrahedron Lett. 1999, 40, 5365-5368.
20. The structure of MAO is not known (linear, ring, and cage structures have all been proposed). Structure 4 is given for conceptual purposes only. For lead overviews, see: a) E. Zurek, T. Ziegler, Prog. Polym. Sci. 2004, 29, 107-148; b) P. L. Bryant, C. R. Harwell, A. A. Mrse, E. F. Emery, Z. Gan, T. Caldwell, A. P. Reyes, P. Kuhns, D. W. Hoyt, L. S. Simeral, R. W. Hall, L. G. Butler, J. Am. Chem. Soc. 2001, 123, 12009-12017; c) H. Hanawa, N. Abe, K. Marouka, Tetrahedron Lett. 1999, 40, 5365-5368.
21. 2) has been reported by the groups of Fu and others, see: a) M. Fontes, X. Verdaguer, L. Solà, M. A. Pericàs, A. Riera, J. Org. Chem. 2004, 69, 2532-2543; b) J. Rudolph, N. Hermanns, C Bolm, J. Org. Chem. 2004, 69, 3997-4000; c) P. I. Dosa, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 445-446; d) P. I. Dosa, J. C. Ruble, G. C. Fu, J. Org. Chem. 1997, 62, 444-445. We are unaware of any work on the equivalent halide equilibrium.
22. 2) has been reported by the groups of Fu and others, see: a) M. Fontes, X. Verdaguer, L. Solà, M. A. Pericàs, A. Riera, J. Org. Chem. 2004, 69, 2532-2543; b) J. Rudolph, N. Hermanns, C Bolm, J. Org. Chem. 2004, 69, 3997-4000; c) P. I. Dosa, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 445-446; d) P. I. Dosa, J. C. Ruble, G. C. Fu, J. Org. Chem. 1997, 62, 444-445. We are unaware of any work on the equivalent halide equilibrium.
23. 2) has been reported by the groups of Fu and others, see: a) M. Fontes, X. Verdaguer, L. Solà, M. A. Pericàs, A. Riera, J. Org. Chem. 2004, 69, 2532-2543; b) J. Rudolph, N. Hermanns, C Bolm, J. Org. Chem. 2004, 69, 3997-4000; c) P. I. Dosa, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 445-446; d) P. I. Dosa, J. C. Ruble, G. C. Fu, J. Org. Chem. 1997, 62, 444-445. We are unaware of any work on the equivalent halide equilibrium.
24. 2) has been reported by the groups of Fu and others, see: a) M. Fontes, X. Verdaguer, L. Solà, M. A. Pericàs, A. Riera, J. Org. Chem. 2004, 69, 2532-2543; b) J. Rudolph, N. Hermanns, C Bolm, J. Org. Chem. 2004, 69, 3997-4000; c) P. I. Dosa, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 445-446; d) P. I. Dosa, J. C. Ruble, G. C. Fu, J. Org. Chem. 1997, 62, 444-445. We are unaware of any work on the equivalent halide equilibrium.
25. -1 < 0.002 under unpromoted conditions: D. F. Evans, G. V. Fazakerley, J. Chem. Soc. A 1971, 182-183;
26. b) Very recently, Knochel has demonstrated exchange of ArZnI species: F. F. Kneisel, M. Dochnahl, P. Knochel, Angew. Chem. 2004, 116, 1032-1036; Angew. Chem. Int. Ed. 2004, 43, 1017-1021.
27. b) Very recently, Knochel has demonstrated exchange of ArZnI species: F. F. Kneisel, M. Dochnahl, P. Knochel, Angew. Chem. 2004, 116, 1032-1036; Angew. Chem. Int. Ed. 2004, 43, 1017-1021.
28. G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748-2749.
29. N. Inguimbert, P. Coric, H. Poras, H. Meudal, F. Teffot, M.-C. Fournie-Zaluski, B. P. Roques, J. Med. Chem. 2002, 45, 1477-1486. Angew. Chem. Int. Ed. 2005, 44, 2237-2241
30. N. Inguimbert, P. Coric, H. Poras, H. Meudal, F. Teffot, M.-C. Fournie-Zaluski, B. P. Roques, J. Med. Chem. 2002, 45, 1477-1486. Angew. Chem. Int. Ed. 2005, 44, 2237-2241