Enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]hept- 5-enes by hetero Diels-Alder addition to cyclopentadiene

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5663-5666

  Blanco, José M ^a   Caamaño, Olga ^a   Fernández, Franco ^a   García Mera, Xerardo ^a   López, Carmen ^a   Rodríguez, Gonzalo ^b   Rodríguez Borges, José E ^a   Rodríguez Hergueta, Antonio ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZABICYCLO[2.2.1]HEPT 5 ENE; CYCLOPENTADIENE DERIVATIVE; NORBORNANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; EXTRACTION; STEREOISOMERISM; SYNTHESIS;

BETULACEAE; STAPHYLOCOCCUS PHAGE 3A;

EID: 0032581748     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01102-2     Document Type: Article

References (26)

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14. 3) signals [3a, 2.78 δ (s, 4-H); 3b, 2.84 δ (s, 4-H), 3c and/or 3d, 3.25 δ (s, 4-H)].
15. d 4.3 Hz), 3. 84 (1H, s), 3.56 and 3.38 (2H, AB system, J 13.1 Hz), 2.78 (1H, s), 1.97-1.84 (2H, m), 1.87 (1H, s), 1.79 (1H, d, J 8.3 Hz), 1.60-1.39 (3H, m), 1.28 (1H, d, J 8.3 Hz), 1.09 (3H, s), 1.08 (3H, s), 1.06-0.73 (3H, m), 0.85 (3H, d, J 6.5 Hz) The X-ray data for 3a will be presented in a separate, full paper.
16. d 4.3 Hz), 3.70 and 3.67 (2H, AB system, J 13.0 Hz), 3.28 (1H, s), 2.21 (1H, d, J 3.7 Hz), 2.14 (1H, s), 1.99-1.82 (3H, m), 1.76 (1H, dd, J 9.5, 1.7 Hz), 1.69-0.75 (10H, m), 1.13 (3H, s), 1.10 (3H, s), 0.85 (3H, d, J 6.5 Hz).
17. 2O led to similar results.
18. 2O exch.), 3.32 (1H, d, J 13 0 Hz), 3.25 (1H, s), 3.11 (1H, s), 298 (1H, d, J 13.0 Hz), 222 (1H, s), 2.07-1.98 (1H, m), 1.94 (1H, d, J 9.8 Hz), 1.61-1.38 (2H, m), 1.33-1.22 (1H, m), 0.97 (1H, d, J 9.8 Hz).
19. 15. Monson, R. S.; Priest, D. N. J. Org. Chem., 1971, 36, 3826.
20. d 4.5), 1.26 (1H, d, J 9.0 Hz).
21. 17. Van Rheenen, V. J. Chem. Soc., Chem. Comm., 1969, 314.
22. 3), δ: 7.35-7.24 (5H, m), 4.68 (1H, d, J 15.1 Hz), 3.93 (1H, d, J 15.1 Hz), 3.68 (1H, s), 2.85 (1H, dd, J 3.8, 1.5 Hz), 1.90-1.82 (1H, m), 1.82 (1H, dd, J 9.4), 1.72-1.47 (3H, m), 1.33 (1H, d, J 9.4 Hz).
23. 1 1.1 Hz).
24. 3).
25. 21. Prof P.M. Cullis kindly supplied us with a sample of 1b obtained by enzymatic resolution of racemic lactam. See: Taylor, S. J. C.; McCague, R.; Wisdom, R.; Lee, C.; Dickson, K.; Ruecroft, G.; O'Brien, F.; Littlechild, J.; Bevan, J.; Roberts, S. M.; Evans, C. T. Tetrahedron: Asymmetry, 1993, 4, 1117).
26. 30-133 (c 0.26, MeOH)].