Practical Asymmetric Synthesis of Vicinal Diamines through the Catalytic Highly Enantioselective Alkylation of Glycine Amide Derivatives

Angewandte Chemie - International Edition

Volumn 42, Issue 47, 2003, Pages 5868-5870

  Ooi, Takashi ^a   Sakai, Daiki ^a   Takeuchi, Mifune ^a   Tayama, Eiji ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alkyl halides; Alkylation; Asymmetric catalysis; Phase transfer catalysis; Vicinal diamines

Indexed keywords

CATALYSIS; DERIVATIVES; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY;

AMINES;

ALKYL GROUP; DIAMINE DERIVATIVE; GLYCINAMIDE; QUATERNARY AMMONIUM DERIVATIVE;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HYDROLYSIS; PHASE TRANSITION; REACTION ANALYSIS;

EID: 0346158950     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352658     Document Type: Article

References (45)

1. E. T. Michalson, J. Szmuszkovicz, Prog. Drug Res. 1989, 33, 135.
2. See, for example: A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517; Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
3. See, for example: A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517; Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
4. For an excellent recent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724; Angew. Chem. Int. Ed. 1998, 37, 2581, and references therein;
5. For an excellent recent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724; Angew. Chem. Int. Ed. 1998, 37, 2581, and references therein;
6. for selected leading references, see also: b) A. Alexakis, I. Aujard, P. Mangeney, Synlett 1998, 873;
7. c) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863;
8. d) P. Saravanan, A. Bisai, S. Baktharaman, M. Chandrasekhar, V. K. Singh, Tetrahedron 2002, 58, 4693.
9. For some impressive contributions, see: a) D. Enders, R. Schiffers, Synthesis 1996, 53, and references therein;
10. b) K. Yamada, S. J. Harwood, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 3713; Angew. Chem. Int. Ed. 1999, 38, 3504.
11. b) K. Yamada, S. J. Harwood, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 3713; Angew. Chem. Int. Ed. 1999, 38, 3504.
12. a) G. Buono, C. Triantaphylides, G. Peiffer, F. Petit, Synthesis 1982, 1030;
13. b) H. Brunner, M. Schmidt, G. Unger, H. Schönenberger, Eur. J. Med. Chem. 1985, 20, 509;
14. c) B. E. Rossiter, M. Eguchi, G. Miao, N. M. Swingle, A. E. Hernández, D. Vickers, E. Fluckiger, R. G. Patterson, K. V. Reddy, Tetrahedron 1993, 49, 965.
15. For recent examples, see: a) G. Guillena, C. Nájera, J. Org. Chem. 2000, 65, 7310, and references therein;
16. b) H. J. Kim, S.-k. Lee, Y. S. Park, Synlett 2001, 613.
17. For the synthetic utility of this type of ammonium salts as chiral phase-transfer catalysts, see: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519;
18. b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228;
19. c) T. Ooi, M. Kameda, H. Tannai, K. Maruoka, Tetrahedron Lett. 2000, 41, 8339;
20. d) T. Ooi, M. Takeuchi, K. Maruoka, Synthesis 2001, 1716;
21. e) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621; Angew. Chem. Int. Ed. 2002, 41, 1551;
22. e) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621; Angew. Chem. Int. Ed. 2002, 41, 1551;
23. f) T. Ooi, M. Takahashi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 2002, 124, 7640;
24. g) T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 4724; Angew. Chem. Int. Ed. 2002, 41, 4542;
25. g) T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 4724; Angew. Chem. Int. Ed. 2002, 41, 4542;
26. h) T. Ooi, E. Tayama, K. Maruoka, Angew. Chem. 2003, 115, 599; Angew. Chem. Int. Ed. 2003, 42, 579.
27. h) T. Ooi, E. Tayama, K. Maruoka, Angew. Chem. 2003, 115, 599; Angew. Chem. Int. Ed. 2003, 42, 579.
28. For excellent reviews on the use of Schiff bases of glycine derivatives, see: a) T. Abellán, R. Chinchilla, N. Galindo, G. Guillena, C. Nájera, J. M. Sansano, Eur. J. Org. Chem. 2000, 2689;
29. b) M. J. O'Donnell, Aldrichimica Acta 2001, 34, 3.
30. Cyclopentyl methyl ether, kindly supplied by Zeon Corporation, Japan, has a higher boiling point (106 °C) than tert-butyl methyl ether. Both ethers are regarded as a potential substitute for diethyl ether.
31. No loss of enantiomeric excess was observed, as determined by HPLC analysis.
32. The catalytic enantioselective preparation of α-amino acid derivatives that contain a tertiary β carbon atom from glycine anion equivalents is commonly regarded as extremely difficult. For a diastereoselective approach, see: a) J. M. McIntosh, R. K. Leavitt, P. Mishra, K. C. Cassidy, J. E. Drake, R. Chadha, J. Org. Chem. 1988, 53, 1947;
33. b) W. Oppolzer, R. Moretti, C. Zhou, Helv. Chim. Acta 1994, 77, 2363;
34. c) D. Seebach, M. Hoffmann, Eur. J. Org. Chem. 1998, 1337;
35. d) S. D. Bull, S. G. Davies, A. C. Garner, N. Mujtaba, Synlett 2001, 781.
36. 11a] an extra reaction step is sometimes necessary, for example, alkylation with a reactive secondary allylic halide and subsequent reduction; see: e) J. M. McIntosh, R. K. Leavitt, Tetrahedron Lett. 1986, 27, 3839.
37. An alternative solution to this long-standing problem is based on elegant boron alkylation chemistry: M. J. O'Donnell, M. D. Drew, J. T. Cooper, F. Delgado, C. Zhou, J. Am. Chem. Soc. 2002, 124, 9348;
38. see also: M. J. O'Donnell, J. T. Cooper, M. M. Mader, J. Am. Chem. Soc. 2003, 125, 2370.
39. 2 as the solvent at -78°C to -40°C did not lead to the formation of the product, and 2b (R=iPr) was obtained in approximately 23 % yield, although with only 7 % ee, after 5 h at -20°C.
40. The absolute configuration of the product 8 was determined to be R by X-ray crystallographic analysis after conversion into a dipeptide with N-benzyloxycarbonyl-L-alanine; see Supporting Information.
41. For the importance of optically active α-amino amides, see, for example: a) A. Rockwell, M. Melden, R. A. Copeland, K. Hardman, C. P. Decicco, W. F. DeGrado, J. Am. Chem. Soc. 1996, 118, 10337;
42. b) K. Kaljuste, J. P. Tam, Tetrahedron Lett. 1998, 39, 9327;
43. c) G. Liu, N. S. Kozmina, M. Winn, T. W. von Geldern, W. J. Chiou, D. B. Dixon, B. Nguyen, K. C. Marsh, T. J. Opgenorth, J. Med. Chem. 1999, 42, 3679;
44. d) M. J. Fray, M. F. Burslem, R. P. Dickinson, Bioorg. Med. Chem. Lett. 2001, 11, 567.
45. E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12414.