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4544229291
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The thermal Alder reaction, in the absence of a transition metal, has had few applications in organic synthesis, due to limitations in scope, particularly as extremely high temperatures are required.
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A. Goeke, M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1996, 108, 686; Angew. Chem. Int. Ed. Engl. 1996, 35, 662 [trap = 2,2″-bis[1- (diarylphosphanyl)-ethyl]-1,1″-biferrocene].
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Goeke, A.1
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A. Goeke, M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1996, 108, 686; Angew. Chem. Int. Ed. Engl. 1996, 35, 662 [trap = 2,2″-bis[1- (diarylphosphanyl)-ethyl]-1,1″-biferrocene].
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M. Hatano, M. Terada, K. Mikami, Angew. Chem. 2001, 113, 255; Angew. Chem. Int. Ed. 2001, 40, 249 [binap = 2,2′-bis(diphenylphosphanyl)-1, 1′-binaphthyl), chiraphos = 2,3-bis(diphenylphosphanyl)butane, diop = 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphanyl)butane].
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M. Hatano, M. Terada, K. Mikami, Angew. Chem. 2001, 113, 255; Angew. Chem. Int. Ed. 2001, 40, 249 [binap = 2,2′-bis(diphenylphosphanyl)-1, 1′-binaphthyl), chiraphos = 2,3-bis(diphenylphosphanyl)butane, diop = 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphanyl)butane].
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P. Cao, X. Zhang, Angew. Chem. 2000, 112, 4270; Angew. Chem. Int. Ed. 2000, 39, 4104 [duphos = 1,2-bis(phospholano)benzene, bicp = 2,2′-bis(diphenylphosphanyl)-1,1′-dicyclopentane, bicpo = 2,2′-bis(diphenylphosphinite)-1,1′-dicyclopentane].
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P. Cao, X. Zhang, Angew. Chem. 2000, 112, 4270; Angew. Chem. Int. Ed. 2000, 39, 4104 [duphos = 1,2-bis(phospholano)benzene, bicp = 2,2′-bis(diphenylphosphanyl)-1,1′-dicyclopentane, bicpo = 2,2′-bis(diphenylphosphinite)-1,1′-dicyclopentane].
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A. Lei, M. He, S. Wu, X. Zhang, Angew. Chem. 2002, 114, 3607; Angew. Chem. Int. Ed. 2002, 41, 4104.
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A. Lei, J. P. Waldkirch, M. He, X. Zhang, Angew. Chem. 2002, 114, 4708; Angew. Chem. Int. Ed. 2002, 41, 4526.
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0035900318
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Pd-catalyzed asymmetric cyclization of similar enynes initiated by acetoxypalladation results in β-deacetoxypalladation (elimination). This protocol is very useful for the asymmetric synthesis of substituted γ-butyrolactones, see: a) Q. Zhang, X. Lu, X. Han, J. Org. Chem. 2001, 66, 7676;
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H. Chakrapani, C. Liu, R. A. Widenhoefer, Org. Lett. 2003, 5, 157. It was found that Rh/binap complexes were not effective catalysts for cyclization/ hydrosilation. [biphemp = 6,6′-bis-(diphenylphosphanyl)-2,2′- dimethyl-biphenyll.
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Org. Lett.
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Chakrapani, H.1
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0038296931
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and references therein
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for a related article, see: d) M. Mori, N. Saito, D. Tanaka, M. Takimoto, Y. Sato, J. Am. Chem. Soc. 2003, 125, 5606 and references therein.
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note
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The presence of phosphane ligands with this catalyst might slow down the rate of cycloisomerization.
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M. Méndez, M. P. Muñuz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511.
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