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4143079275
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Conjugate addition reactions of terminal acetylenes using late transition metal catalysts (Rh, Ru, Pd) have been documented. However, these reactions are limited to β-unsubstituted vinyl ketones or acrylates. See: (a) Lerum, R. V.; Chisholm, J. D. Tetrahedron Lett. 2004, 45, 6591-6594.
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9144270060
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Chen, L.1
Li, C.-J.2
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14
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0037099395
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A similar catalyst was used for the copper-catalyzed Huisgen reaction. See: Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
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15
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9344245165
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Knöpfel, T. F.; Aschwanden, P.; Ichikawa, T.; Watanabe, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2004, 43, 5971-5973.
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Carreira, E.M.5
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16
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22144473432
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note
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For ligand structures and names, see Supporting Information.
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17
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0027408256
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Alock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743-756.
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Alock, N.W.1
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18
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22144488905
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note
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The relative configuration of the ligand 7 was unambiguously established by X-ray crystallographic analysis (ref 18).
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19
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22144467819
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note
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The absolute configuration of the ascorbate has no effect on the asymmetric induction; in the addition to 1a using (+)-ascorbate, 7 and ent-7 furnished enantiomeric products of identical % ee.
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20
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22144498206
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note
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We found that a 2:1 ligand/copper ratio led to complete inhibition of the reaction.
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21
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22144492009
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CCDC 268029 (4-bromoanilide of 2b) and CCDC 268030 (7) contain the supplementary crystallographic data for this communication. These data can be obtained online free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html (or from Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21 EZ, U.K.; Fax (+44) 1223-336-033; or deposit@cccd.cam.ac.uk).
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22
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22144450772
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Int. Appl. PCT, WO 0009116, 2000
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(a) Xiang, J. N.; Karpinski, J. M.; Christensen, S. B., IV. Int. Appl. PCT, WO 0009116, 2000.
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Christensen IV, S.B.3
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22144461518
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Int. Appl. PCT, WO 0009115, 2000
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(b) Xiang, J. N.; Osifo, I. K.; Karpinski, J. M.; Christensen, S. B., IV. Int. Appl. PCT, WO 0009115, 2000.
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22144434169
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Int. Appl. PCT, WO 9703945, 1997
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Christensen IV, S.B.1
Karpinski, J.M.2
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25
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17644414186
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2O; for a mechanistic study involving related Cu(I) acetylides, see: Valentin, O.; Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 44, 2210-2215.
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