Planar chirality: Synthesis and transannular reactions of unsaturated optically active azoninones bearing E-olefins

Journal of Organic Chemistry

Volumn 65, Issue 6, 2000, Pages 1710-1720

  Sudau, Alexander ^a   Munch, Winfried ^a   Nubbemeyer, Udo ^a   Bats, Jan W ^b  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; LACTAM DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; OPTICAL ROTATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034708730     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991484o     Document Type: Article

References (56)

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34. The stereochemical terminology concerning the azoninones is used according to Eliel, E. L.; Wilen, S. H.; Mander; L. N. Stereochemistry of Organic Compounds; J. Wiley: New York, 1994; p 1121 (nomenclature pS, pR) and p 1203 (trans cycloalkenes). Description of trans cycloalkenes as planar chiral compounds: Schlögl, K. Top. Curr. Chem. 1984, 125, 27 and Nakazaki, M.; Yamamoto, K.; Naemura, K. Top. Curr. Chem. 1984, 125, 1. Alternative description as axial chiral compounds: Krow, G. Top. Stereochem. 1970, 5, 31.
35. The stereochemical terminology concerning the azoninones is used according to Eliel, E. L.; Wilen, S. H.; Mander; L. N. Stereochemistry of Organic Compounds; J. Wiley: New York, 1994; p 1121 (nomenclature pS, pR) and p 1203 (trans cycloalkenes). Description of trans cycloalkenes as planar chiral compounds: Schlögl, K. Top. Curr. Chem. 1984, 125, 27 and Nakazaki, M.; Yamamoto, K.; Naemura, K. Top. Curr. Chem. 1984, 125, 1. Alternative description as axial chiral compounds: Krow, G. Top. Stereochem. 1970, 5, 31.
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37. 1. For further data see Supporting Information and Figure 2.
38. The NMR spectra of lactam 5a showed a doubled set of peaks, indicating the existence of two major diastereomeric species (ratio 3:1, independent of the temperature), and an additional minor conformer (about 5%). Several attempts to separate the compounds by means of HPLC failed because of the rapid adjustment of the equilibrium state. NOE analyses proved the conformation 5a (first major diastereomer). The second major conformation might be the structure 5c as shown in the Figure 4, but the NOE data left some doubts. The third compound could have represented a further lactam with an anti arrangement of C-3 and C-9 in respect to the partial double bond.
39. Related effects had been reported investigating Xenicane diterpenes: (a) Guella, G.; Chiasera, G.; N'Diaye, I.; Pietra, F. Helv. Chim. Acta 1994, 77, 1203. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 5546 (indolizidines).
40. Related effects had been reported investigating Xenicane diterpenes: (a) Guella, G.; Chiasera, G.; N'Diaye, I.; Pietra, F. Helv. Chim. Acta 1994, 77, 1203. (b) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 5546 (indolizidines).
41. -1 (±3).
42. 3 near the C-4/ C-5 double bond showed this bond to be slightly disordered. A careful inspection of the data showed two possible orientations for this bond: a major orientation with an occupancy factor of about 0.88 (6b in Figure 3) and a minor orientation with an occupancy factor of about 0.12 (resulting from cocrystallized 6a, Figure 2).
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50. Force field calculations of cyclic 1,5-nonadienes were reported by White, D. N. J.; Bowill, M. J. J. Chem. Soc., Perkin Trans. 2 1977, 1610.
51. -1, half-life period at 133°C: 120 h. Cope, A. C.; Pawson, B. A. Ibid. 1965, 87, 3649.
52. -1, half-life period at 133°C: 120 h. Cope, A. C.; Pawson, B. A. Ibid. 1965, 87, 3649.
53. 2 followed an exceptional path despite varying reaction conditions: The selective formation of 11a failed; only varying mixtures of 11a and 11c have been found to give predominantly lactam 11c.
54. Force field MM+ calculations had been carried out with Hyperchem arranging C-3 and C-9 cis with respect to the double bond character of the lactam unit. The structures are outlined in Figure 4. Transannular distances of type-c-conformation (N-C-5/N-C-6, [Å]): 4c: 3.3/2.98, 5c: 3.35/3.03, 6c: 3.34/3.04.
55. -1) than the trans/cis structures discussed above. Nevertheless, the existence of such structures as reactive (and diastereomeric) intermediates/transition states in the transannular ring contractions yielding a or c type products could neither be excluded nor proven. However, the presumption that diastereomeric properties caused the formation of the different bicycles was left as is. The determination of the transannular distances of N-C-5/N-C-6 would have allowed a very similar argumentation.
56. Nubbemeyer, U. Synthesis 1993, 1120.