Diastereoselective synthesis of γ-amino acids and their derivatives from nitroethane via intermediacy of 5,6-dihydro-4H-1,2-oxazines bearing the CH2CH(CO2Me)2 substituent at C3

Synthesis

Volumn , Issue 5, 2009, Pages 741-754

  Sukhorukov, Alexey Yu ^a   Lesiv, Alexey V ^a   Khomutova, Yulia A ^a   Ioffe, Sema L ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

amino acids; 2 oxazines, reduction; 5,6 dihydro 4h 1; Oxyiminium cations

Indexed keywords

2-OXAZINES, REDUCTION; 5,6-DIHYDRO-4H-1; DIASTEREOSELECTIVE SYNTHESIS; MALONATES; OXYIMINIUM CATIONS; SODIUM CYANOBOROHYDRIDE; STEREO-SELECTIVE; TWO-STEP REDUCTIONS;

AMINATION; AMINES; AMINO ACIDS; POSITIVE IONS; STEREOCHEMISTRY;

ORGANIC ACIDS;

5,6 DIHYDRO 4H 1,2 OXAZINE DERIVATIVE; AMINO ACID DERIVATIVE; DIMETHYL 2 [[1 (TERT BUTOXYCARBONYL) 3 (4 METHOXYPHENYL) 5 METHYLPYRROLIDIN 2 YL]METHYL]MALONATE; DIMETHYL 2 [[2 BENZOYL 4 (4 METHOXYPHENYL) 6 PHENYLTETRAHYDRO 2H 1,2 OXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [ 2 (BENZOYLAMINO) 5 HYDROXY 3,5 DIMETHYLHEXYL]MALONATE; DIMETHYL REL 2 [ 2 (BENZOYLAMINO) 5 HYDROXY 5 METHYL 3 PHENYLHEXYL]MALONATE; DIMETHYL REL 2 [2 (BENZOYLAMINO) 3 (4 METHOXYPHENYL) 5 PHENYLPENTYL]MALONATE; DIMETHYL REL 2 [2 (BENZOYLAMINO) 5 HYDROXY 3 (4 METHOXYPHENYL) 5 METHYLHEXYL]MALONATE; DIMETHYL REL 2 [[1 (TERT BUTOXYCARBONYL) 3 (4 METHOXYPHENYL)PYRROLIDIN 2 YL]METHYL]MALONATE; DIMETHYL REL 2 [[2 (BENZOYLAMINO) 3 [2 HYDROXYCYCLOHEXYL] 3 (4 METHOXYPHENYL]PROPYL]MALONATE; DIMETHYL REL 2 [[2 BENZOYL 4 (4 CHLOROPHENYL) 6,6 DIMETHYLTETRAHYDRO 2H 1,2 OXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [[2 BENZOYL 4 (4 METHOXYPHENYL) 6 PHENYLTETRAHYDRO 2H 1,2 OXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [[2 BENZOYL 4 (4 METHOXYPHENYL) 6,6 DIMETHYLTETRAHYDRO 2H 1,2 OXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [[2 BENZOYL 4 (4 METHOXYPHENYL)OCTAHYDRO 2H 1,2 BENZOXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [[2 BENZOYL 4,6,6 TRIMETHYLTETRAHYDRO 2H 1,2 OXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [[2 BENZOYL 6,6 DIMETHYL 1,4 PHENYLTETRAHYDRO 2H 1,2 OXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [[4 (4 METHOXYPHENYL) 6 PHENYL 5,6 DIHYDRO 4H 1,2 OXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [[4 (4 METHOXYPHENYL) 6,6 DIMETHYL TETRAHYDRO 2H 1,2 OXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [[6 ETHOXY 4 (4 METHOXYPHENYL)TETRAHYDRO 2H 1,2 OXAZIN 3 YL]METHYL]MALONATE; DIMETHYL REL 2 [[6 METHOXY 4 (4 METHOXYPHENYL) 6 METHYLTETRAHYDRO 2H 1,2 OXAZIN 3 YL]METHYL]MALONATE; GAMMA AMINO ACID; METHYL 2 ETHOXY 4 (4 METHOXYPHENYL) 7 OXOHEXAHYDRO 2H PYRROLO[1,2 B][1,2]OXAZINE 6 CARBOXYLATE; METHYL 2,2 DIMETHYL 7 OXO 4 PHENYLHEXAHYDRO 2H PYRROLO[1,2 B][1,2]OXAZINE 6 CARBOXYLATE; METHYL 2,2,4 TRIMETHYL 7 OXOHEXAHYDRO 2H PYRROLO[1,2 B][1,2]OXAZINE 6 CARBOXYLATE; METHYL 4 (4 CHLOROPHENYL) 2,2 DIMETHYL 7 OXOHEXAHYDRO 2H PYRROLO[1,2 B][1,2]OXAZINE 6 CARBOXYLATE; METHYL 4 (4 METHOXYPHENYL) 2,2 DIMETHYL 7 OXOHEXAHYDRO 2H PYRROLO[1,2 B][1,2]OXAZINE 6 CARBOXYLATE; OXAZINE DERIVATIVE; REL 3[3 (4 METHOXYPHENYL) 5 METHYLPYRROLIDIN 2 YL]PROPANOIC ACID; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL BOND; REDUCTION; STEREOCHEMISTRY;

EID: 63449132892     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083360     Document Type: Article

References (45)

1. (a) Hipelli, C.; Reissig, H.-U. Liebigs Ann. Chem. 1990, 475.
2. (b) Paulini, K.; Gerold, A.; Reissig, H.-U. Liebigs Ann. Chem. 1995, 667.
3. Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014.
4. Zimmer, R.; Collas, M.; Czerwonka, R.; Hain, U.; Reissig, H.-U. Synthesis 2008, 237.
5. (a) Hippeli, C.; Zimmer, R.; Reissig, H.-U. Liebigs Ann. Chem. 1990, 469.
6. (b) Nakanishi, S.; Otsuji, Y.; Itoh, K.; Hayashi, N. Bull. Chem. Soc. Jpn. 1990, 63, 3595.
7. Nakanishi, S.; Shirai, Y.; Takahashi, K.; Otsuji, Y. Chem. Lett. 1981, 869.
8. Chrystal, E. J. T.; Gilchrist, T. L.; Stretch, W. J. Chem. Res., Synop. 1987, 180; J. Chem. Res., Miniprint 1987, 1563.
9. Zimmer, R.; Collas, M.; Roth, M.; Reissig, H.-U. Liebigs Ann. Chem. 1992, 709.
10. (a) Sukhorukov, A. Y.; Lesiv, A. V.; Eliseev, O. L.; Khomutova, Yu. A.; Bondarenko, T. N.; Lapidus, A. L.; Ioffe, S. L. Mendeleev Commun. 2007, 122.
11. (b) Sukhorukov, A. Y.; Lesiv, A. V.; Khomutova, Yu. A.; Ioffe, S. L.; Nelyubina, Y. V. Synthesis 2008, 1205.
12. Sukhorukov, A. Y.; Lesiv, A. V.; Eliseev, O. L.; Khomutova, Yu. A.; Ioffe, S. L.; Borissova, A. O. Eur. J. Org. Chem. 2008, 4025.
13. (a) Henning, R.; Lerch, U.; Urbah, H. Synthesis 1989, 265.
14. (b) Gallos, J. K.; Sarli, V. C.; Massen, Z. S.; Varvogli, A. C.; Papadoyanni, C. Z.; Papaspyrou, S. D.; Argyropoulos, N. G. Tetrahedron 2005, 61, 565.
15. Tishkov, A. A.; Reissig, H.-U.; Ioffe, S. L. Synlett 2002, 863.
16. Lyapkalo, I. M.; Ioffe, S. L. Russ. Chem. Rev. (Engl. Transl.) 1998, 67, 467.
17. (a) Sukhorukov, A. Y.; Klenov, M. S.; Ivashkin, P. E.; Lesiv, A. V.; Khomutova, Yu. A.; Ioffe, S. L. Synthesis 2007, 97.
18. (b) Klenov, M. S.; Lesiv, A. V.; Khomutova, Yu. A.; Nesterov, I. D.; Ioffe, S. L. Synthesis 2004, 1159.
19. Eliseev, O. L.; Ivashkin, P. E.; Ostapenko, A. G.; Lesiv, A. V.; Khomutova, Yu. A.; Ioffe, S. L.; Lapidus, A. L. Synlett 2006, 2239.
20. Zimmer, R.; Arnold, T.; Homann, K.; Reissig, H.-U. Synthesis 1994, 1050.
21. Ivashkin, P. E.; Sukhorukov, A. Y.; Eliseev, O. L.; Lesiv, A. V.; Khomutova, Yu. A.; Ioffe, S. L. Synthesis 2007, 3461.
22. 4, MeOH] in products 10 failed, therefore they could not be used in route c (Scheme 3).
23. 2O nor with CbzCl.
24. 3CN, AcOH, Scheme 9).
25. Successful transformation 6h to 10h can be realized only by heating 6h in AcOH (see experimental part).
26. For similar processes in the hydrogenation of other 6- phenyl-substituted 5,6-dihydro-4H-1,2-oxazines see ref. 3.
27. (a) Ben-Ishai, D.; Altman, J.; Peled, N. Tetrahedron 1977, 33, 2715.
28. (b) Ohkuma, T.; Ishii, D.; Takeno, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 6510.
29. Lauer, W. M.; Lockwood, R. G. J. Am. Chem. Soc. 1954, 76, 3974.
30. Boger, D. L.; Machiya, K. J. Am. Chem. Soc. 1992, 114, 10056.
31. (e) Gutzwiller, J.; Uskokovic, M. J. Am. Chem. Soc. 1970, 92, 204.
32. Reduction of iminium salt 15c to tetrahydrooxazine 6c is accompanied by the partial formation of oxime ether 4c (yield: 25%).
33. Buchholz, M.; Reissig, H.-U. Eur. J. Org. Chem. 2003, 3524.
34. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
35. Lambert, J. B.; Takeuchi, Y. Cyclic Organonitrogen Stereodynamics; VCH: New York, 1992, Chap 7.1.1 and 7.2.1, and references cited therein.
36. Nesterov, I. D.; Lesiv, A. V.; Ioffe, S. L.; Antpin, M. Yu. Mendeleev Commun. 2004, 280.
37. (a) Smirnov, V. O.; Ioffe, S. L.; Tishkov, A. A.; Khomutova, Yu. A.; Nesterov, I. D.; Antpin, M. Yu.; Smit, W. A.; Tartakovsky, V. A. J. Org. Chem. 2004, 69, 8485.
38. (b) Khomutova, Yu. A.; Smirnov, V. O.; Mayr, H.; Ioffe, S. L. J. Org. Chem. 2007, 72, 9134.
39. It is noteworthy, that according to NMR cation 15c and its precursor, dihydrooxazine 4c, have the same dominant conformation.
40. 10 can be also rationalized in terms of proximal approach of the reducing agent to the cation intermediate.
41. An example of such a process is discussed in ref. 23a.
42. (a) Ponomarev, A. A.; Noritsina, M. V.; Krivenko, A. P. Chem. Heterocycl. Compd. (Engl. Transl.) 1970, 978.
43. (b) Fulep, G. H.; Hoesl, C. E.; Hofner, G.; Wanner, K. T. Eur. J. Med. Chem. 2006, 41, 809.
44. Vara Prasad, J. V. N.; Loo, J. A.; Boyer, F. E.; Stier, M. A.; Gogliotti, R. D.; Turner, W. J.; Harvey, P. J.; Kramer, M. R.; Mack, D. P.; Scholten, J. D.; Gracheck, S. J.; Domagala, J. M. Bioorg. Med. Chem. 1998, 6, 1707.
45. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512.