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2. Solé, D.; Cancho, Y.; Llebaria, A.; Moretó, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904.
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Delgado, A.5
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4. For a review on the use of aminoacid and derivatives thereof in asymmetric synthesis, see: Ager, D. A.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
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5
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0010662182
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note
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2CN moiety.
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6
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0029928957
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13CNMR could also be used as a diagnostic tool, since Δδ around 3 ppm were observed. For a related empirical use of chemical shift differences for stereochemical assignments in related compounds, see Hashimoto, K.; Konno, K.; Shirahama, H. J. Org. Chem. 1996, 61, 4685-4692.
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University Science Books: Mill Valley, California
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7. Collman, J.; Hegedus, L.; Norton, G.; Finke, G. Principles and Applications of Organotransition Metal Chemistry.; University Science Books: Mill Valley, California, 1987.
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Principles and Applications of Organotransition Metal Chemistry
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Collman, J.1
Hegedus, L.2
Norton, G.3
Finke, G.4
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8
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0001200603
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8. In order to explain the high or complete diastereoselectivity observed for substrates bearing an ester (1g and 1h) or a carbamate group (1i) (entries 7-9, Table 1), an additional attractive interaction between the side chain carbonyl group and the nitrogen lone pair could also be considered. Attractive interaction N→C=O has been demonstrated both in solid state and in solution; see, for example: a) Schweizer, W.B.; Procter, G.; Kaftory, M.; Dunitz; J.D. Helv. Chim. Acta , 1978, 61, 2783-2808;
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Schweizer, W.B.1
Procter, G.2
Kaftory, M.3
Dunitz, J.D.4
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0001578322
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c) Leonard, N.J.; Morrow, D.F.; Rogers, M.T. J. Am. Chem. Soc. 1957, 79, 5476-5479;
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Leonard, N.J.1
Morrow, D.F.2
Rogers, M.T.3
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11
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0031575584
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and references cited therein. Additional examples where this type of interaction has also been invoked: Selectivity control in Diels-Alder reactions
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d) Leonard, N.J. Tetrahedron., 1997, 53, 2325-2355 and references cited therein. Additional examples where this type of interaction has also been invoked: Selectivity control in Diels-Alder reactions:
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Leonard, N.J.1
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e) Cordes, M.H.J.; de Gala, S.; Berson, J.A. J. Am. Chem. Soc. 1994, 116, 11161-11162;
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Cordes, M.H.J.1
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Conformational equilibrium related to bioactivity of certain analgesics
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g) Bachrach, S.M. J. Org. Chem. 1995, 60, 4395-4398. Conformational equilibrium related to bioactivity of certain analgesics:
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Bachrach, S.M.1
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Correlation with the geometry of nucleophile approach on the attack to carbonyl or nitrile groups
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h) Bürgi, H.B.; Dunitz, J.D.; Shefter, E. Nature new Biol., 1973, 244, 186-188. Correlation with the geometry of nucleophile approach on the attack to carbonyl or nitrile groups:
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Bürgi, H.B.1
Dunitz, J.D.2
Shefter, E.3
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i) Bürgi, H.B.; Dunitz, J.D.; Shefter, E. J. Am. Chem. Soc., 1973, 61, 2783-2808;
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j) Baxter, P.W.N.; Connor, J.A.; Povey, D.C.; Wallis, J.D. J. Chem. Soc., Chem Commun. 1991,1135-1137.
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9. Owczarczyk, Z.; Lamaty, F.; Vawter, E. J.; Negishi, E. J. Am. Chem. Soc. 1992, 114, 10091-10092.
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Owczarczyk, Z.1
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0010743779
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note
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11. In agreement with our previous results, cyclization of 1k under standard conditions afforded a complex mixture in which no trace (formula presented) of the desired cycloadduct 2 could be detected. However, this result indicates the inability of the side chain acetate carbonyl group to stabilize by coordination an alkylnickel intermediate such as 2′ (see Figure 3).
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21
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0001069897
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12. Although in 3c and in 3e, a vinylnickel-carbonyl coordination could be the origin of the diastereoselection, we have been unable to find a likely explanation for our experimental results based on this hypothesis. For coordination of carbonyl groups with the metal center in organometallic nickel compounds, see: a) Sacerdoti, M.; Bertolasi, V.; Gilli, G. Acta Crystallogr. 1980, B36, 1061;
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Sacerdoti, M.1
Bertolasi, V.2
Gilli, G.3
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22
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84985521835
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b) Schröder, W.; Pörschke, K.R.; Tsay, Y.-H.; Krüger, C. Angew. Chem. Int. Ed. Engl., 1987, 26, 919-921;
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Schröder, W.1
Pörschke, K.R.2
Tsay, Y.-H.3
Krüger, C.4
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23
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0001368713
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c) Carmona, E.; Gutiérrez-Puebla, E.; Monge, A.; Marín, J.M.; Paneque, M.; Poveda, M.L. Organometallics, 1989,8, 967-975.
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Carmona, E.1
Gutiérrez-Puebla, E.2
Monge, A.3
Marín, J.M.4
Paneque, M.5
Poveda, M.L.6
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24
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0025280370
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For conformational effects due to nickel-carbonyl chelation, see: d) Shambayati, S.; Crowe, W.E.; Schreiber, S.L. Angew. Chem. Int. Ed. Engl., 1990, 29, 256-272.
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Shambayati, S.1
Crowe, W.E.2
Schreiber, S.L.3
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