Regioselective palladium-catalyzed allylic alkylations via anti/syn-π-allyl intermediates

Synlett

Volumn , Issue 4, 2004, Pages 623-626

  Kazmaier, Uli ^a   Pohlman, Matthias ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Allylic alkylation; Amino acids; Chelated enolates; Palladium; isomerization

Indexed keywords

ALLYL COMPOUND; AMINO ACID; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHELATION; CHEMICAL REACTION; ISOMERIZATION; SYNTHESIS; TEMPERATURE;

EID: 1642377774     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817776     Document Type: Article

References (35)

1. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Book: Herndon, 1999.
2. For a detailed survey of palladium-catalyzed reactions, see: Malleron, J. C.; Fiaud, J. C.; Legros, J. Y. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: San Diego, 1997.
3. Reviews: (a) Godleski, S. A. Comprehensive Organic Synthesis, Vol 4; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon; Oxford, 1991, 585-661. (b) Lübbers, T.; Metz, P. Hauben Weyl: Methoden der organischen Chemie - Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart/New York, 1996, 2371-2473. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705; and references cited therein.
4. Reviews: (a) Godleski, S. A. Comprehensive Organic Synthesis, Vol 4; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon; Oxford, 1991, 585-661. (b) Lübbers, T.; Metz, P. Hauben Weyl: Methoden der organischen Chemie - Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart/New York, 1996, 2371-2473. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705; and references cited therein.
5. Reviews: (a) Godleski, S. A. Comprehensive Organic Synthesis, Vol 4; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon; Oxford, 1991, 585-661. (b) Lübbers, T.; Metz, P. Hauben Weyl: Methoden der organischen Chemie - Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart/New York, 1996, 2371-2473. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705; and references cited therein.
6. Reviews: (a) Godleski, S. A. Comprehensive Organic Synthesis, Vol 4; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon; Oxford, 1991, 585-661. (b) Lübbers, T.; Metz, P. Hauben Weyl: Methoden der organischen Chemie - Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart/New York, 1996, 2371-2473. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705; and references cited therein.
7. (a) Kazmaier, U. Curr. Org. Chem. 2003, 317.
8. (b) Kazmaier, U.; Pohlman, M. In Metal Catalyzed C-C and C-N Coupling Reactions; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim,,, in press; and references cited therein.
9. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
10. The syn/anti terminology is used to describe the orientation of the substituents on the allyl moiety relative to the H-atom at the central carbon atom.
11. Corradini, P.; Maglio, G.; Musco, A.; Paiaro, G. J. Chem. Soc., Chem. Commun. 1966, 618.
12. An early example for an allylation of ketone enolates with retention of configuration was described by: Lui, F.-T.; Negishi, E.-I. J. Org. Chem. 1985, 50, 4762.
13. For iridium catalyzed reactions with retention of olefin geometry see: (a) Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647. (b) Takeuchi, R.; Shiga, N. Org. Lett. 1999, 265. (c) Takeuchi, R.; Tanabe, K. Angew. Chem. Int. Ed. 2000, 39, 1975; Angew. Chem. 2000, 112, 2051.
14. For iridium catalyzed reactions with retention of olefin geometry see: (a) Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647. (b) Takeuchi, R.; Shiga, N. Org. Lett. 1999, 265. (c) Takeuchi, R.; Tanabe, K. Angew. Chem. Int. Ed. 2000, 39, 1975; Angew. Chem. 2000, 112, 2051.
15. For iridium catalyzed reactions with retention of olefin geometry see: (a) Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647. (b) Takeuchi, R.; Shiga, N. Org. Lett. 1999, 265. (c) Takeuchi, R.; Tanabe, K. Angew. Chem. Int. Ed. 2000, 39, 1975; Angew. Chem. 2000, 112, 2051.
16. For iridium catalyzed reactions with retention of olefin geometry see: (a) Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647. (b) Takeuchi, R.; Shiga, N. Org. Lett. 1999, 265. (c) Takeuchi, R.; Tanabe, K. Angew. Chem. Int. Ed. 2000, 39, 1975; Angew. Chem. 2000, 112, 2051.
17. For reduction of p-allyl palldium complexes at low temperature with retention of olefin geometry see:Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 2918.
18. Reviews: (a) Kazmaier, U. Amino Acids 1996, 11, 283. (b) Kazmaier, U. Liebigs Ann. Recl. 1997, 285. (c) Kazmaier, U. Recent Res. Devel. Org. Chem. 1998, 2, 351.
19. Reviews: (a) Kazmaier, U. Amino Acids 1996, 11, 283. (b) Kazmaier, U. Liebigs Ann. Recl. 1997, 285. (c) Kazmaier, U. Recent Res. Devel. Org. Chem. 1998, 2, 351.
20. Reviews: (a) Kazmaier, U. Amino Acids 1996, 11, 283. (b) Kazmaier, U. Liebigs Ann. Recl. 1997, 285. (c) Kazmaier, U. Recent Res. Devel. Org. Chem. 1998, 2, 351.
21. (a) Kazmaier, U.; Zumpe, F. L. Angew. Chem. Int. Ed. 1999, 38, 1468; Angew. Chem. 1999, 111, 1572.
22. (a) Kazmaier, U.; Zumpe, F. L. Angew. Chem. Int. Ed. 1999, 38, 1468; Angew. Chem. 1999, 111, 1572.
23. (b) Weiß, T. D.; Helmchen, G.; Kazmaier, U. Chem. Commun. 2002, 1270.
24. (a) Kazmaier, U.; Zumpe, F. L. Angew. Chem. Int. Ed. 2000, 39, 802; Angew. Chem. 2000, 112, 805.
25. (a) Kazmaier, U.; Zumpe, F. L. Angew. Chem. Int. Ed. 2000, 39, 802; Angew. Chem. 2000, 112, 805.
26. (b) Kazmaier, U.; Zumpe, F. L. Eur. J. Org. Chem. 2001, 4067.
27. R(syn-8) = 22.93′. The syn-configured reference samples required were obtained by chelate-Claisen-rearrangement according to: Kazmaier, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998; Angew. Chem. 1994, 106, 1046.
28. R(syn-8) = 22.93′. The syn-configured reference samples required were obtained by chelate-Claisen-rearrangement according to: Kazmaier, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998; Angew. Chem. 1994, 106, 1046.
29. 2. CCDC 221039 contains the supplemetary crystallographic data of 11. The data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44(1223)336033 or deposit@ccdc.cam.ac.uk).
30. For discussions concerning the memory effect see: (a) Trost, B. M.; Bunt, R. C. J Am. Chem. Soc. 1996, 118, 235. (b) Hayashi, T.; Kawatsura, M.; Kozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (c) Lloyd-Jones, G. C.; Stephen, S. C. Chem.-Eur. J. 1998, 4, 2539. (d) Acemoglu, L.; Williams, J. M. J. Adv. Synth. Catal. 2001, 343, 75. (e) Fairlamb, I. J. S.; Lloyd-Jones, G. C.; Stephan, V.; Kocovsky, P. Chem.-Eur. J. 2002, 8, 4443. (f) Gais, H. J.; Jagusch, T.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Chem.-Eur. J. 2003, 9, 4202.
31. For discussions concerning the memory effect see: (a) Trost, B. M.; Bunt, R. C. J Am. Chem. Soc. 1996, 118, 235. (b) Hayashi, T.; Kawatsura, M.; Kozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (c) Lloyd-Jones, G. C.; Stephen, S. C. Chem.-Eur. J. 1998, 4, 2539. (d) Acemoglu, L.; Williams, J. M. J. Adv. Synth. Catal. 2001, 343, 75. (e) Fairlamb, I. J. S.; Lloyd-Jones, G. C.; Stephan, V.; Kocovsky, P. Chem.-Eur. J. 2002, 8, 4443. (f) Gais, H. J.; Jagusch, T.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Chem.-Eur. J. 2003, 9, 4202.
32. For discussions concerning the memory effect see: (a) Trost, B. M.; Bunt, R. C. J Am. Chem. Soc. 1996, 118, 235. (b) Hayashi, T.; Kawatsura, M.; Kozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (c) Lloyd-Jones, G. C.; Stephen, S. C. Chem.-Eur. J. 1998, 4, 2539. (d) Acemoglu, L.; Williams, J. M. J. Adv. Synth. Catal. 2001, 343, 75. (e) Fairlamb, I. J. S.; Lloyd-Jones, G. C.; Stephan, V.; Kocovsky, P. Chem.-Eur. J. 2002, 8, 4443. (f) Gais, H. J.; Jagusch, T.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Chem.-Eur. J. 2003, 9, 4202.
33. For discussions concerning the memory effect see: (a) Trost, B. M.; Bunt, R. C. J Am. Chem. Soc. 1996, 118, 235. (b) Hayashi, T.; Kawatsura, M.; Kozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (c) Lloyd-Jones, G. C.; Stephen, S. C. Chem.-Eur. J. 1998, 4, 2539. (d) Acemoglu, L.; Williams, J. M. J. Adv. Synth. Catal. 2001, 343, 75. (e) Fairlamb, I. J. S.; Lloyd-Jones, G. C.; Stephan, V.; Kocovsky, P. Chem.-Eur. J. 2002, 8, 4443. (f) Gais, H. J.; Jagusch, T.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Chem.-Eur. J. 2003, 9, 4202.
34. For discussions concerning the memory effect see: (a) Trost, B. M.; Bunt, R. C. J Am. Chem. Soc. 1996, 118, 235. (b) Hayashi, T.; Kawatsura, M.; Kozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (c) Lloyd-Jones, G. C.; Stephen, S. C. Chem.-Eur. J. 1998, 4, 2539. (d) Acemoglu, L.; Williams, J. M. J. Adv. Synth. Catal. 2001, 343, 75. (e) Fairlamb, I. J. S.; Lloyd-Jones, G. C.; Stephan, V.; Kocovsky, P. Chem.-Eur. J. 2002, 8, 4443. (f) Gais, H. J.; Jagusch, T.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Chem.-Eur. J. 2003, 9, 4202.
35. For discussions concerning the memory effect see: (a) Trost, B. M.; Bunt, R. C. J Am. Chem. Soc. 1996, 118, 235. (b) Hayashi, T.; Kawatsura, M.; Kozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (c) Lloyd-Jones, G. C.; Stephen, S. C. Chem.-Eur. J. 1998, 4, 2539. (d) Acemoglu, L.; Williams, J. M. J. Adv. Synth. Catal. 2001, 343, 75. (e) Fairlamb, I. J. S.; Lloyd-Jones, G. C.; Stephan, V.; Kocovsky, P. Chem.-Eur. J. 2002, 8, 4443. (f) Gais, H. J.; Jagusch, T.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Chem.-Eur. J. 2003, 9, 4202.