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1,3-Dipolar Cycloadditions
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G. Thieme, Stuttgart
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(Eds.: H. R. Rzepa, J. Syndner). (CD-ROM); Royal Society of Chemistry Publications
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R. Annunziata, M. Benaglia, M Cinquini, F. Cozzi, L. Raimondi, in Electronic Conference on Heterocyclic Chemistry (ECHET96). (Eds.: H. R. Rzepa, J. Syndner). (CD-ROM); Royal Society of Chemistry Publications, 1996 (see also: http://www.ch.ic.ac.uk/ectoc/echet96/papers/026/index.htm). CD-ROM included in J. Chem. Soc., Chem. Commun 1997, no. 6. Very recently, the attribution of the syn 4,4′ relative stereochemistry was confirmed on similar compounds via X-Ray analysis: M. Martín-Vilà. N. Hanafi, J. M. Jiménez, A. Alvarez-Lorena, J. F. Piniella, V. Branchadell, A. Oliva, R. M. Ortuño, J. Org. Chem 1998, 63, 3581.
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12
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R. Annunziata, M. Benaglia, M Cinquini, F. Cozzi, L. Raimondi, in Electronic Conference on Heterocyclic Chemistry (ECHET96). (Eds.: H. R. Rzepa, J. Syndner). (CD-ROM); Royal Society of Chemistry Publications, 1996 (see also: http://www.ch.ic.ac.uk/ectoc/echet96/papers/026/index.htm). CD-ROM included in J. Chem. Soc., Chem. Commun 1997, no. 6. Very recently, the attribution of the syn 4,4′ relative stereochemistry was confirmed on similar compounds via X-Ray analysis: M. Martín-Vilà. N. Hanafi, J. M. Jiménez, A. Alvarez-Lorena, J. F. Piniella, V. Branchadell, A. Oliva, R. M. Ortuño, J. Org. Chem 1998, 63, 3581.
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R. Annunziata, M. Benaglia, M Cinquini, F. Cozzi, L. Raimondi, in Electronic Conference on Heterocyclic Chemistry (ECHET96). (Eds.: H. R. Rzepa, J. Syndner). (CD-ROM); Royal Society of Chemistry Publications, 1996 (see also: http://www.ch.ic.ac.uk/ectoc/echet96/papers/026/index.htm). CD-ROM included in J. Chem. Soc., Chem. Commun 1997, no. 6. Very recently, the attribution of the syn 4,4′ relative stereochemistry was confirmed on similar compounds via X-Ray analysis: M. Martín-Vilà. N. Hanafi, J. M. Jiménez, A. Alvarez-Lorena, J. F. Piniella, V. Branchadell, A. Oliva, R. M. Ortuño, J. Org. Chem 1998, 63, 3581.
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Jiménez, J.M.3
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Piniella, J.F.5
Branchadell, V.6
Oliva, A.7
Ortuño, R.M.8
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14
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0025975617
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15
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0000862693
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[8a] R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi. Tetrahedron 1987, 43, 4051.
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16
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0000810833
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[8b] R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, J. Org. Chem. 1990, 55, 1901.
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17
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2842574998
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-
note
-
The inside alkoxy cycloadduct features a 5,5′-syn (not anti) relative configuration because of the different priorities of the substituents at the C-5.
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-
-
-
18
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33845283500
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-
All cycloadditions were performed in benzene as solvent (Experimental Section and note 20) Alkene 3 was reacted with formaldehyde N-benzylnitrone in DMSO as solvent (80°C, 2 h, 50%). The diastereoisomeric ratio (15a/b ≥ 85:15) was the same observed for the reaction performed in benzene, thus ruling out the presence of an hydrogen bond within the reactants in the TS. The presence of a H bond between the OH and the π bond in the ground state conformation of allylic alcohols was suggested: S. D. Kahn, C. F. Pau, A. R. Chamberlin, W. J. Hehre J. Am. Chem. Soc. 1987, 109, 650.
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Kahn, S.D.1
Pau, C.F.2
Chamberlin, A.R.3
Hehre, W.J.4
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19
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0002343032
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[11a] V. Jäger, I. Müller, R. Schohe, M. Frey, R. Ehrler, B. Häfele, D. Schröter, Lect. Heterocycl. Chem. 1985, 8, 79.
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Jäger, V.1
Müller, I.2
Schohe, R.3
Frey, M.4
Ehrler, R.5
Häfele, B.6
Schröter, D.7
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20
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2842552690
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-
Unpublished results from our laboratories
-
[11b] Unpublished results from our laboratories.
-
-
-
-
21
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0000524047
-
-
For recent results in this field, see: F. Busqué, P. de March, M. Figueredo, J. Font, M. Monsalvatje, A. Virgili, A, Alvarez-Larena, J. F. Piniella, J. Org. Chem 1996, 61, 8578.
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Busqué, F.1
De March, P.2
Figueredo, M.3
Font, J.4
Monsalvatje, M.5
Virgili, A.6
Alvarez-Larena, A.7
Piniella, J.F.8
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22
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0030200947
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For related results, see: G. Galley, P. G. Jones, M. Pätzel, Tetrahedron: Asymmetry 1996, 7, 2073.
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(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 2073
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Galley, G.1
Jones, P.G.2
Pätzel, M.3
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23
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0001562620
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[14a] Y. Yamamoto, Y. Chounan, S. Nishii, T. Ibuka, H. Kitahara, J. Am Chem. Soc. 1992, 114, 7652.
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Yamamoto, Y.1
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Kitahara, H.5
-
24
-
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0030734550
-
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[14b] For a recent study on Michael-type addition to (E)- and (Z)-γ-alkoxy-α,β-unsaturated esters leading to a prevalence of syn adducts, see:Y. Xiang, H.-J. Gi, D. Niu, R. F. Schinazi, K. Zhao, J. Org. Chem. 1997, 62, 7430.
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Xiang, Y.1
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Zhao, K.5
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25
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0023043811
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-
[15a] K. N. Houk M. N. Paddon-Row, N. G. Rondan. Y.-D. Wu, F. K. Brown, D. C. Spellmeyer, J. T. Metz, Y. Li, R. J. Loncharich, Science 1986, 231, 1108.
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Science
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Houk, K.N.1
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Wu, Y.-D.4
Brown, F.K.5
Spellmeyer, D.C.6
Metz, J.T.7
Li, Y.8
Loncharich, R.J.9
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27
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0003323222
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Molecular Mechanics
-
American Chemical Society; Washington D.C.
-
U. Burkert, N. L. Allinger, Molecular Mechanics. ACS Monograph 177; American Chemical Society; Washington D.C., 1982.
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ACS Monograph 177
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Burkert, U.1
Allinger, N.L.2
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28
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84986437005
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F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J Comput. Chem. 1990, 11, 440.
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Mohamadi, F.1
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Liskamp, R.4
Lipton, M.5
Caufield, C.6
Chang, G.7
Hendrickson, T.8
Still, W.C.9
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31
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2842573876
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-
note
-
Cycloaddition reactions were performed in benzene on a reduced scale. Special care is needed, since this solvent is known to be highly toxic and carcinogenic.
-
-
-
-
35
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2842599329
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-
MacroModel substructures can be obtained directly from the authors (e-mail: laura@iumchz.chimorg.unimi.it)
-
MacroModel substructures can be obtained directly from the authors (e-mail: laura@iumchz.chimorg.unimi.it).
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