Generation of functional diversity via nitroaldol condensations of α-aminoacid aldehydes - A new and stereocontrolled route to acyclic 1,3-diamino-2-alcohols

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 987-990

  Hanessian, Stephen ^a   Devasthale, Pratik V ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AMINOALCOHOL; DIAMINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030032947     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02359-3     Document Type: Article

References (26)

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2. Henry, L. C. R. Acad. Sci. 1895, 120, 1265; Henry, L. Bull. Soc. Chim. Fr. 1895, 13, 999; Houben-Weyl-Muller, Methoden der Organischen Chemie, 4th ed., Bd. 10/1. Thieme, Stuttgart, 1971, pp 246; Baer, H.; Urbas, L. in Feuer, H: The Chemistry of Nitro and Nitroso Groups, Interscience, New York 1970, 75; Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1; Combes, R. G. in "Comprehensive Organic Chemistry", Barton, D. H. R.; Ollis, W. D., eds. Pergamon, Oxford, 1979, vol. 2, p 348.
3. Henry, L. C. R. Acad. Sci. 1895, 120, 1265; Henry, L. Bull. Soc. Chim. Fr. 1895, 13, 999; Houben-Weyl-Muller, Methoden der Organischen Chemie, 4th ed., Bd. 10/1. Thieme, Stuttgart, 1971, pp 246; Baer, H.; Urbas, L. in Feuer, H: The Chemistry of Nitro and Nitroso Groups, Interscience, New York 1970, 75; Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1; Combes, R. G. in "Comprehensive Organic Chemistry", Barton, D. H. R.; Ollis, W. D., eds. Pergamon, Oxford, 1979, vol. 2, p 348.
4. Henry, L. C. R. Acad. Sci. 1895, 120, 1265; Henry, L. Bull. Soc. Chim. Fr. 1895, 13, 999; Houben-Weyl-Muller, Methoden der Organischen Chemie, 4th ed., Bd. 10/1. Thieme, Stuttgart, 1971, pp 246; Baer, H.; Urbas, L. in Feuer, H: The Chemistry of Nitro and Nitroso Groups, Interscience, New York 1970, 75; Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1; Combes, R. G. in "Comprehensive Organic Chemistry", Barton, D. H. R.; Ollis, W. D., eds. Pergamon, Oxford, 1979, vol. 2, p 348.
5. Henry, L. C. R. Acad. Sci. 1895, 120, 1265; Henry, L. Bull. Soc. Chim. Fr. 1895, 13, 999; Houben-Weyl-Muller, Methoden der Organischen Chemie, 4th ed., Bd. 10/1. Thieme, Stuttgart, 1971, pp 246; Baer, H.; Urbas, L. in Feuer, H: The Chemistry of Nitro and Nitroso Groups, Interscience, New York 1970, 75; Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1; Combes, R. G. in "Comprehensive Organic Chemistry", Barton, D. H. R.; Ollis, W. D., eds. Pergamon, Oxford, 1979, vol. 2, p 348.
6. Henry, L. C. R. Acad. Sci. 1895, 120, 1265; Henry, L. Bull. Soc. Chim. Fr. 1895, 13, 999; Houben-Weyl-Muller, Methoden der Organischen Chemie, 4th ed., Bd. 10/1. Thieme, Stuttgart, 1971, pp 246; Baer, H.; Urbas, L. in Feuer, H: The Chemistry of Nitro and Nitroso Groups, Interscience, New York 1970, 75; Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1; Combes, R. G. in "Comprehensive Organic Chemistry", Barton, D. H. R.; Ollis, W. D., eds. Pergamon, Oxford, 1979, vol. 2, p 348.
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12. Rosini, G.; Ballini, R.; Sorrenti, P. Synthesis 1983, 1014.
13. Fernández, R.; Gasch, C.; Gómez-Sánchez, A.; Vflchez, J. E.; Castro, A. L.; Diánez, M. J.; Estrada, M. D.; Pérez-Garrido, S. Carbohydr. Res. 1993, 247, 239.
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17. For a recent report on nitroaldol condensations of α-amino aldehydes, see: Sasai, H.; Kim, W-S.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1994, 35, 6123.
18. 4Cl, extracted into ether and processed as usual. Flash chromatography (10% ethyl acetate-hexanes) yielded 10 mg of the syn isomer and 95 mg of the anti isomer 1h (63 % total).
19. 3: 1a: -0.13 °(0.115); 1b: 24.4 °(c 0.36); 1c: -30.0 °(0.09); 1d: -40.0 °(0.25); 1e: -7.4 ° (0.14); 1f: +11.0 °(0.78); 1g: +8.79 °(2.0); anti-1h: +10.8 °(1.14); syn-1h: +22.33 °(0.22). melting points for crystalline products in °C: 1a: 98-100; 1c: 104-105; 1d: 128-130; 1e: 110-112; 1h (anti): 109-111; 1h (syn): 115-116.
20. 2) showed a coupling constant of 2 Hz between H-3 and H-4, suggesting a trans relationship.
21. X-ray coordinates have been deposited at the Cambridge Crystallographic Data Centre. (formula presented) X-ray crystal structure of 1c X-ray crystal structure of 1d
22. 3N, we obtained a 97:3 mixture in 22% yield.
23. Pirkle, W. H.; Hoover, D. J. Top. Stereochem. 1982, 13, 263.
24. Seebach, D.; Beck, A. K.; Mukhopadhyay, T.; Thomas, E. Helv. Chim. Acta 1982, 65, 1102.
25. For an alternative approach to 1,3-diamino-2-ols (anti-syn), see Reetz, M. T.; Wünsch, T.; Harms, K. Tetrahedron: Asymmetry 1990, 1, 371; Reetz, M. T.; Binder, J. Tetrahedron Lett. 1989, 30, 5425.
26. For an alternative approach to 1,3-diamino-2-ols (anti-syn), see Reetz, M. T.; Wünsch, T.; Harms, K. Tetrahedron: Asymmetry 1990, 1, 371; Reetz, M. T.; Binder, J. Tetrahedron Lett. 1989, 30, 5425.