Chiral ligand-controlled diastereoselectivity and regioselectivity in palladium(0)-catalysed allylations

Tetrahedron Letters

Volumn 41, Issue 28, 2000, Pages 5387-5391

  Pyne, Stephen G ^a   Dong, Zemin ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

Allyl ic amine; Allylation; Catalysis; Chiral ligand; Diastereoselection; Malonate; Palladium; Regiochemistry

Indexed keywords

ALLYL COMPOUND; BENZOIC ACID DERIVATIVE; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; STEREOCHEMISTRY;

EID: 0034622390     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00860-1     Document Type: Article

References (28)

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2. For other examples, see: (a) Bäckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826. (b) Reetz, M. T.; Wang, F.; Harms, K. J. Chem. Soc., Chem. Commun. 1991, 1309. (c) Arai, M.; Nemoto, T.; Ohashi, Y.; Nakamura, E. Synlett 1992, 309. (d) Vettal, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849. (e) Sato, T.; Kido, M.; Otera, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2254. (f) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293. (g) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (h) Pyne, S. G.; Dong, Z. Tetrahedron Lett. 1999, 40, 6131.
3. For other examples, see: (a) Bäckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826. (b) Reetz, M. T.; Wang, F.; Harms, K. J. Chem. Soc., Chem. Commun. 1991, 1309. (c) Arai, M.; Nemoto, T.; Ohashi, Y.; Nakamura, E. Synlett 1992, 309. (d) Vettal, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849. (e) Sato, T.; Kido, M.; Otera, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2254. (f) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293. (g) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (h) Pyne, S. G.; Dong, Z. Tetrahedron Lett. 1999, 40, 6131.
4. For other examples, see: (a) Bäckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826. (b) Reetz, M. T.; Wang, F.; Harms, K. J. Chem. Soc., Chem. Commun. 1991, 1309. (c) Arai, M.; Nemoto, T.; Ohashi, Y.; Nakamura, E. Synlett 1992, 309. (d) Vettal, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849. (e) Sato, T.; Kido, M.; Otera, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2254. (f) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293. (g) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (h) Pyne, S. G.; Dong, Z. Tetrahedron Lett. 1999, 40, 6131.
5. For other examples, see: (a) Bäckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826. (b) Reetz, M. T.; Wang, F.; Harms, K. J. Chem. Soc., Chem. Commun. 1991, 1309. (c) Arai, M.; Nemoto, T.; Ohashi, Y.; Nakamura, E. Synlett 1992, 309. (d) Vettal, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849. (e) Sato, T.; Kido, M.; Otera, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2254. (f) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293. (g) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (h) Pyne, S. G.; Dong, Z. Tetrahedron Lett. 1999, 40, 6131.
6. For other examples, see: (a) Bäckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826. (b) Reetz, M. T.; Wang, F.; Harms, K. J. Chem. Soc., Chem. Commun. 1991, 1309. (c) Arai, M.; Nemoto, T.; Ohashi, Y.; Nakamura, E. Synlett 1992, 309. (d) Vettal, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849. (e) Sato, T.; Kido, M.; Otera, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2254. (f) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293. (g) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (h) Pyne, S. G.; Dong, Z. Tetrahedron Lett. 1999, 40, 6131.
7. For other examples, see: (a) Bäckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826. (b) Reetz, M. T.; Wang, F.; Harms, K. J. Chem. Soc., Chem. Commun. 1991, 1309. (c) Arai, M.; Nemoto, T.; Ohashi, Y.; Nakamura, E. Synlett 1992, 309. (d) Vettal, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849. (e) Sato, T.; Kido, M.; Otera, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2254. (f) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293. (g) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (h) Pyne, S. G.; Dong, Z. Tetrahedron Lett. 1999, 40, 6131.
8. For other examples, see: (a) Bäckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826. (b) Reetz, M. T.; Wang, F.; Harms, K. J. Chem. Soc., Chem. Commun. 1991, 1309. (c) Arai, M.; Nemoto, T.; Ohashi, Y.; Nakamura, E. Synlett 1992, 309. (d) Vettal, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849. (e) Sato, T.; Kido, M.; Otera, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2254. (f) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. Tetrahedron Lett. 1996, 37, 9293. (g) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (h) Pyne, S. G.; Dong, Z. Tetrahedron Lett. 1999, 40, 6131.
9. (a) Trost, B. M.; Vanvranken, D. L. Chem. Rev. 1996, 96, 395.
10. (b) Williams, J. M. J. Synlett 1996,705.
11. (c) Pfaltz, A. Synlett 1999, 835.
12. (d) Helmchen, G. J. Organomet. Chem. 1999, 576, 203.
13. (a) Hilgraf, R.; Pfaltz, A. Synlett 1999, 1814.
14. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545.
15. For studies on other chiral substrates, see: (a) Ref. 1(g and h). (b) Michelet, V.; Besnier, V.; Genet, J. P. Synlett 1996, 215. (c) Michelet, V.; Genet, J. P. Bull. Soc. Chim. Fr. 1996, 133, 881. (d) Atlan, V.; Racouchot, S.; Rubin, M.; Bremer, C.; Ollivier, J.; de Meijere, A.; Salaun, J. Tetrahedron: Asymmetry 1998, 9, 1131. (e) Cook, G. R.; Shanker, P. S.; Pararajasingham, K. Angew. Chem., Int. Ed. Engl. 1999, 38, 110.
16. For studies on other chiral substrates, see: (a) Ref. 1(g and h). (b) Michelet, V.; Besnier, V.; Genet, J. P. Synlett 1996, 215. (c) Michelet, V.; Genet, J. P. Bull. Soc. Chim. Fr. 1996, 133, 881. (d) Atlan, V.; Racouchot, S.; Rubin, M.; Bremer, C.; Ollivier, J.; de Meijere, A.; Salaun, J. Tetrahedron: Asymmetry 1998, 9, 1131. (e) Cook, G. R.; Shanker, P. S.; Pararajasingham, K. Angew. Chem., Int. Ed. Engl. 1999, 38, 110.
17. For studies on other chiral substrates, see: (a) Ref. 1(g and h). (b) Michelet, V.; Besnier, V.; Genet, J. P. Synlett 1996, 215. (c) Michelet, V.; Genet, J. P. Bull. Soc. Chim. Fr. 1996, 133, 881. (d) Atlan, V.; Racouchot, S.; Rubin, M.; Bremer, C.; Ollivier, J.; de Meijere, A.; Salaun, J. Tetrahedron: Asymmetry 1998, 9, 1131. (e) Cook, G. R.; Shanker, P. S.; Pararajasingham, K. Angew. Chem., Int. Ed. Engl. 1999, 38, 110.
18. For studies on other chiral substrates, see: (a) Ref. 1(g and h). (b) Michelet, V.; Besnier, V.; Genet, J. P. Synlett 1996, 215. (c) Michelet, V.; Genet, J. P. Bull. Soc. Chim. Fr. 1996, 133, 881. (d) Atlan, V.; Racouchot, S.; Rubin, M.; Bremer, C.; Ollivier, J.; de Meijere, A.; Salaun, J. Tetrahedron: Asymmetry 1998, 9, 1131. (e) Cook, G. R.; Shanker, P. S.; Pararajasingham, K. Angew. Chem., Int. Ed. Engl. 1999, 38, 110.
19. For studies on other chiral substrates, see: (a) Ref. 1(g and h). (b) Michelet, V.; Besnier, V.; Genet, J. P. Synlett 1996, 215. (c) Michelet, V.; Genet, J. P. Bull. Soc. Chim. Fr. 1996, 133, 881. (d) Atlan, V.; Racouchot, S.; Rubin, M.; Bremer, C.; Ollivier, J.; de Meijere, A.; Salaun, J. Tetrahedron: Asymmetry 1998, 9, 1131. (e) Cook, G. R.; Shanker, P. S.; Pararajasingham, K. Angew. Chem., Int. Ed. Engl. 1999, 38, 110.
20. 3). Compound 2: 6.43 (1H, d, J=16.0), 6.15 (1H, dd, J=16.0, 10.4), 4.21 (2H, q, J=7.2), 4.04 (4H, m), 3.72 (1H, d, J=11.2), 2.88 (1H, dt, J=10.4, 2.0), 1.28 (3H, t, J=7.2), 1.12 (3H, d, J=6.0), 1.10 (3H, t, J=7.2); compound 3: 5.72 (1H, dd, J=7.4, 1.2), 0.84 (9H, s); compound 4: 5.77 (1H, dd, J=7.4, 2.0), 0.86 (9H, s); compound 8: 6.48 (1H, d, J=16.2), 6.10 (1H, dd, J=16.2, 8.4), 3.94 (1H, m), 3.92 (1H, d, J=13.8), 3.65 (1H, d, J=13.8), 3.18 (1H, dd, J=9.0, 3.6), 2.89 (1H, m), 1.16 (3H, d, J=6.3); compound 9: 5.67 (2H, m), 4.31 (1H, m), 4.21 (1H, m), 3.72 (2H, d, J=4.2), 1.21 (3H, d, J=6.3); compound 10: 5.68 (2H, m), 4.29 (1H, m), 4.20 (1H, m), 3.73 (2H, m), 1.19 (3H, d, J=6.7); compound 11: 6.51 (1H, d, J=16.5), 6.03 (1H, dd, J=16.5, 8.7), 3.89 (1H, d, J=13.2), 3.80 (1H, m), 3.65 (1H, d, J=13.2), 3.07 (1H, dd, J=8.1, 8.1), 1.16 (3H, d, J=6.3).
21. Both (R)-BINAP and 5 give the same enantiomeric product in the Pd(0)-catalysed reactions of racemic PhCH(OAc)CH=CHPh with malonate, see: Ref. 2b and Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493.
22. Details will be published in a full paper.
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27. For other allylic aminations using 5, see: Vonmatt, P.; Loiseleur, O.; Koch, G.; Pfaltz, A.; Lefeber, C.; Feucht, T.; Helmchen, G. Tetrahedron: Asymmetry 1994, 5, 573.
28. von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Ruegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265.