Palladium-catalyzed enantioselective alkylative ring opening [2]

Journal of the American Chemical Society

Volumn 122, Issue 8, 2000, Pages 1804-1805

  Lautens, Mark ^a   Renaud, Jean Luc ^a   Hiebert, Sheldon ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM;

ALKYLATION; CHEMICAL STRUCTURE; ENANTIOMER; LETTER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034104304     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993427i     Document Type: Letter

References (40)

1. a) Lautens, M.; Rovis, T. J. Am. Chem. Soc. 1997, 119, 11090.
2. (b) Lautens, M.; Rovis, T. Tetrahedron 1998, 54, 1107.
3. (c) Lautens, M.; Ma, S.; Chiu, P. J. Am. Chem. Soc. 1997, 119, 6478.
4. (d) Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532.
5. (e) Lautens, M.; Chiu, P.; Colucci, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 281.
6. Lautens, M.; Rovis, T. J. Org. Chem. 1997, 62, 5246.
7. Kamal, A.; Gayatri, N. L. Tetrahedron Lett. 1996, 37, 3359 and references therein.
8. Snyder, S. E.; et al. J. Med. Chem. 1995, 38, 2395.
9. Kim, K.; Guo, Y.; Sulikowski, G. A. J. Org. Chem. 1995, 60, 6866.
10. (a) Lautens, M.; Klute, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 442.
11. (b) Arjona, O.; de Dios, A.; Fernandez de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906.
12. (c) Lautens, M.; Abd-El-Aziz, A. S.; Lough, A. J. Org. Chem. 1990, 55, 5305.
13. (d) Lautens, M.; Di Felice, C.; Huboux, A. Tetrahedron Lett. 1989, 30, 6817.
14. Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954.
15. (g) (a) Lautens, M. Synlett 1993, 177-185.
16. (b) Chiu, P.; Lautens, M. Topics Curr. Chem. 1997, 190, 1.
17. a) Duan, J. P.; Cheng, C. H. Tetrahedron Lett. 1993, 34, 4019.
18. (b) Duan, J. P.; Cheng, C. H. Organometallics 1995, 14, 1608.
19. (c) Feng, C.-C.; Nandi, M.; Sambaiah, T.; Cheng, C. H. J. Org. Chem. 1999, 64, 3538.
20. Moinet, C.; Fiaud, J. C. Tetrahedron Lett. 1995, 36, 2051.
21. Fugami, K.; Hagiwara, S.; Oda, H.; Kosugi, M. Synlett 1998, 477.
22. Caple, R.; Chen, G. M. S.; Nelson, J. D. J. Org. Chem. 1971, 36, 2874.
23. Lautens, M.; Gadja, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193.
24. (a) Lautens, M.; Ma, S. J. Org. Chem. 1996, 61, 7246.
25. (b) Ma, S. Ph.D. Thesis, University of Toronto, 1996.
26. 3Al and bis(neoisomenthylindenyl)zirconium dichloride as a chiral catalyst; private communication.
27. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.
28. A ligand study will be published in a forthcoming full paper.
29. For the preparation and use of (4S)-2-(2-(diphenylphosphino)phenyl)-4-isopropyl-1,3-oxazoline (abbreviated as i-Pr-POX), see: (a) Williams, J. M. J. Synlett 1996, 705 and references therein. (b) Spinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (c) Von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. For a review on oxazolines and bisoxazolines, see: (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (e) Pfaltz, A. Synlett 1999, 835.
30. For the preparation and use of (4S)-2-(2-(diphenylphosphino)phenyl)- 4-isopropyl-1,3-oxazoline (abbreviated as i-Pr-POX), see: (a) Williams, J. M. J. Synlett 1996, 705 and references therein. (b) Spinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (c) Von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. For a review on oxazolines and bisoxazolines, see: (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (e) Pfaltz, A. Synlett 1999, 835.
31. For the preparation and use of (4S)-2-(2-(diphenylphosphino)phenyl)- 4-isopropyl-1,3-oxazoline (abbreviated as i-Pr-POX), see: (a) Williams, J. M. J. Synlett 1996, 705 and references therein. (b) Spinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (c) Von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. For a review on oxazolines and bisoxazolines, see: (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (e) Pfaltz, A. Synlett 1999, 835.
32. For the preparation and use of (4S)-2-(2-(diphenylphosphino)phenyl)- 4-isopropyl-1,3-oxazoline (abbreviated as i-Pr-POX), see: (a) Williams, J. M. J. Synlett 1996, 705 and references therein. (b) Spinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (c) Von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. For a review on oxazolines and bisoxazolines, see: (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (e) Pfaltz, A. Synlett 1999, 835.
33. For the preparation and use of (4S)-2-(2-(diphenylphosphino)phenyl)- 4-isopropyl-1,3-oxazoline (abbreviated as i-Pr-POX), see: (a) Williams, J. M. J. Synlett 1996, 705 and references therein. (b) Spinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (c) Von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. For a review on oxazolines and bisoxazolines, see: (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1. (e) Pfaltz, A. Synlett 1999, 835.
34. For the synthesis of 2(S)-(diphenylphosphino)-1-[4(S)-isopropyl-2-oxazolin-2-yl]ferrocene (abbreviated as (S)-i-Pr-DIPOF), see: (a) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377. (b) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (c) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. (d) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 62, 10.
35. For the synthesis of 2(S)-(diphenylphosphino)-1-[4(S)-isopropyl-2- oxazolin-2-yl]ferrocene (abbreviated as (S)-i-Pr-DIPOF), see: (a) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377. (b) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (c) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. (d) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 62, 10.
36. For the synthesis of 2(S)-(diphenylphosphino)-1-[4(S)-isopropyl-2- oxazolin-2-yl]ferrocene (abbreviated as (S)-i-Pr-DIPOF), see: (a) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377. (b) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (c) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. (d) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 62, 10.
37. For the synthesis of 2(S)-(diphenylphosphino)-1-[4(S)-isopropyl-2- oxazolin-2-yl]ferrocene (abbreviated as (S)-i-Pr-DIPOF), see: (a) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377. (b) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (c) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. (d) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 62, 10.
38. N2′ mechanism is unlikely. The details will be reported in the full account of this work.
39. (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
40. (b) Pfaltz, A.; Lautens, M. Comp. Asym. Ca. Springer-Verlag, 1999, 833.