A highly stereoselective synthesis of optically active trisubstituted 1,2-ethylenediamines: The first example of Grignard addition to N-diphenylphosphinoyl ketimines derived from amino acids

Journal of Organic Chemistry

Volumn 69, Issue 19, 2004, Pages 6329-6334

  Kohmura, Yoshinori ^a   Mase, Toshiaki ^a  

^a BANYU PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; KETONES; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

Α-AMINO ACIDS; 1,2-ETHYLENEDIAMINES; OPTICAL ACTIVE COMPOUNDS; RACEMIZATION;

AMINES;

1 (4 FLUOROPHENYL) 1 PHENYL 1,2 PROPANEDIAMINE; ALPHA AMINO ACID; ETHYLENEDIAMINE DERIVATIVE; IMINE; N DIPHENYLPHOSPHINOYL KETIMINE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; GRIGNARD REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

AMINO ACIDS; ETHYLENEDIAMINES; IMINES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 4644251195     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049405i     Document Type: Article

References (39)

1. For a recent review of the chemistry of 1,2-ethylenediamines, see: Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627 and references therein.
2. (a) Anastassiadou, M.; Danoun, S.; Crane, L.; Baziard-Mouysset, G.; Payard, M.; Caignard, D.-H.; Rettori, M.-C.; Renard, P. Bioorg. Med. Chem. 2001, 9, 585-592.
3. (b) Szabo, B. Pharmacol. Ther. 2002, 93, 1-35.
4. Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529-13530.
5. (a) For substitution of the hydroxyl group with azide under acidic condition and consecutive hydrogenation, see: Wey, S.-J.; O'Connor, K. J.; Burrows, C. J. Tetrahedron Lett. 1993, 34, 1905-1908.
6. (b) For [3+2] cycloadditions between nonracemic p-toluenesulfinimines and iminoesters, see: Viso, A.; Fernández de la Pradilla, R.; García, A.; Guerrero-Strachan, C.; Alonso, M.; Tortosa, M.; Flores, A.; Martínez-Ripoll, M.; Fonseca, I.; André, I.; Rodríguez, A. Chem. Eur. J. 2003, 9, 2867-2876 and references therein.
7. (c) For stereoselective alkylation of chiral 3-amino-4-styryl-β- lactams, see: Ojima, I.; Pei, Y. Tetrahedron Lett. 1990, 31, 977-980.
8. For a recent review of the construction of quaternary carbon stereocenters, see: Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401 and references therein.
9. (a) Hua, D. H.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4-6.
10. (b) Spero, D. M.; Kapadia, S. R. J. Org. Chem. 1997, 62, 5537-5541.
11. (c) Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268-269.
12. (d) Steinig, A. G.; Spero, D. M. J. Org. Chem. 1999, 64, 2406-2410.
13. (e) Cimarelli, C.; Palmieri, G.; Volpini, E. Tetrahedron: Asymmetry 2002, 13, 2011-2018.
14. (f) Cimarelli, C.; Palmieri, G.; Volpini, E. J. Org. Chem. 2003, 68, 1200-1206.
15. Marco and Carda have reported nucleophilic alkylation to α-oxyketimines derived from erythrulose; see: (a) Marco, J. A.; Carda, M.; Murga, J.; González, F.; Falomir, E. Tetrahedron Lett. 1997, 38, 1841-1844.
16. (b) Marco, J. A.; Carda, M.; Murga, J.; Rodríguez, S.; Falomir, E.; Oliva, M. Tetrahedron: Asymmetry 1998, 9, 1679-1701.
17. (c) Portolés, R.; Murga, J.; Falomir, E.; Carda, M.; Uriel, S.; Marco, J. A. Synlett 2002, 711-714.
18. (a) Wolfe, J. P.; Ney, J. E. Org. Lett. 2003, 5, 4607-4610.
19. (b) Gilman, H.; Eisch, J. J. Am. Chem. Soc. 1957, 79, 2150-2153.
20. Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999; p 598.
21. For a contemporaneous study of addition to N-diphenylphosphinoyl α-ketimino ester, see: Wipf, P.; Stephenson, C. R. J. Org. Lett. 2003, 5, 2449-2452.
22. Davis, F. A.; Haque, M. S.; Przeslawski, R. M. J. Org. Chem. 1989, 54, 2021-2024.
23. Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521-524.
24. It is presumed that slight loss of ee in 4d and 4e would take place at the formation of oximes 3, which required the longer reaction time under reflux condition due to steric bulkiness in 2d and 2e.
25. Stork, G.; Dowd, S. R. J. Am. Chem. Soc. 1963, 85, 2178-2180.
26. 2, and LiBr were used.
27. The main byproduct was corresponding enamide 6.
28. The enantiomeric excesses of the Bz-imines 7da, 7db, and 7ea were the same as those of the substrate imines 4d and 4e. From these results, no enolization occurred because of the bulkiness of the isopropyl group.
29. 8ab and 8ba were prepared by removal of Boc and diphenylphosphinoyl groups from 5ab and 5ba consecutive treatment with 1,1′- carbonyldiimidazole, respectively.
30. We consider that Z-ketimines converted to E-isomers in the reaction system and E-ketimines constructed a five-membered transition structure by coordination of magnesium ion on nitrogen atom to ketimine nitrogen. It is reported that N-diphenylphosphinoyl ketimines exist in a very fast equilibrium between E- and Z-isomers, see: Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634-5635.
31. The diphenylphosphinoyl group is slightly less stable to acid than the Boc group, see ref 9a.
32. 4.
33. (a) Denis, P.; Mortreux, A.; Petit, F.; Buono, G.; Peiffer, G. J. Org. Chem. 1984, 49, 5274-5276.
34. (b) Kolodiazhnyi, O. I.; Gryshkun, E. V.; Andrushko, N. V.; Freytag, M.; Jones, P. G.; Schmutzler, R. Tetrahedron: Asymmetry 2003, 14, 181-183.
35. (a) Takaya, H.; Akutagawa, S.; Noyori, R. Org. Synth. 1988, 67, 20-31.
36. (b) Coumbe, T.; Lawrence, N. J.; Muhammad, F. Tetrahedron Lett. 1994, 35, 625-628.
37. (c) Wang, Y.; Guo, H.; Ding, K. Tetrahedron: Asymmetry 2000, 11, 4153-4162.
38. The assay yield of the desired product in the crude reaction mixture by HPLC did not concur with the isolated yield since isolation of diamines is difficult because of their polar and protic nature (Table 3, entry 1).
39. Stereochemistry was assigned by consideration of the reaction mechanism.