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Volumn 120, Issue 27, 1998, Pages 6661-6672

The stereochemical dichotomy in palladium(0)- and nickel(0)-catalyzed allylic substitution

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

EID: 2642670293     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980222l     Document Type: Article
Times cited : (61)

References (100)
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    • For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190. See also: (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986. 51, 2655. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034. For recent examples, see, e.g.: (e) Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759 and references therein. (f) Breit, B. J. Chem. Soc., Chem. Commun. 1997, 591. (g) Breit, B. Angew. Chem., Int. Ed. 1997, 35, 2835.
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    • For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190. See also: (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986. 51, 2655. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034. For recent examples, see, e.g.: (e) Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759 and references therein. (f) Breit, B. J. Chem. Soc., Chem. Commun. 1997, 591. (g) Breit, B. Angew. Chem., Int. Ed. 1997, 35, 2835.
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    • For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190. See also: (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986. 51, 2655. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034. For recent examples, see, e.g.: (e) Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759 and references therein. (f) Breit, B. J. Chem. Soc., Chem. Commun. 1997, 591. (g) Breit, B. Angew. Chem., Int. Ed. 1997, 35, 2835.
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    • Breit, B.1
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    • note
    • All yields refer to "isolated" yields.
  • 51
    • 84920313107 scopus 로고    scopus 로고
    • note
    • The Mitsunobu reaction using the alcohol obtained on saponification of either acetate 13 or 14 failed to produce the required syn-epimer, giving mainly elimination products.
  • 54
    • 84920313106 scopus 로고    scopus 로고
    • note
    • 2Pd, p-benzoquinone, LiCl, and AcOLi in an AcOH-hexane mixture proved essential for the reaction to proceed with acceptable efficiency, with the formation of the products of the competing Diels-Alder addition of p-BQ to the diene 18 being substantially reduced.
  • 55
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    • Thesis, Royal Institute of Technology, Stockholm
    • 1H NMR, as derived from a large series of compounds, see: Nordberg, R. Thesis, Royal Institute of Technology, Stockholm, 1982. The characteristic features are as follows: chemical shifts of the corresponding allylic protons are consistently higher for the trans-series by ∼0.1 ppm and their W/2 values (width at half-height of the multiplet) are typically twice as large. Thus, (E)-1,4-diacetoxycyclohex-2-ene shows CH-OAc at δ 5.32 (m, W/2 = 11 Hz), whereas its Z-counterpart exhibits this proton at δ 5.23 (m, W/2 = 8 Hz). Analogously, the products of monosubstitution of the latter diacetates with malonate give the following values for the allylic protons: 2.98 (m) and 5.28 (m, W/2 = 16 Hz) for the E-isomer and 2.88 (m) and 5.19 (m, W/2 = 9 Hz) for the Z-isomer. The data obtained for our compounds are in line with this generalization.
    • (1982)
    • Nordberg, R.1
  • 58
    • 84920313105 scopus 로고    scopus 로고
    • note
    • 2 singlet at 5.00 ppm), the corresponding proton in 27a appears at 5.17 ppm as ddd (J = 3, 5.5, and 9 Hz).
  • 59
    • 84920313104 scopus 로고    scopus 로고
    • note
    • n at 29.3, 127.3, and 129.4 ppm.
  • 60
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    • note
    • 22
  • 61
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    • 3-complexes of Pd, see ref 23.
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    • The "Bosnich mechanism" was actually first proposed by Collman and Hegedus: (a) Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; p 692. For further examples, see refs 6b, 8, 23, 26, and (b) Bäckvall, J.-E.; Vågberg, J. O.; Zercher, G.; Genêt, J. P.; Denis, A. J. Org. Chem. 1987, 52, 5430. (c) Moreno-Mañas, M.; Ribas, J.; Virgili, A. J. Org. Chem. 1988, 53, 5328. (d) Kurosawa, H.; Ogoshi, S.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Chem. Lett. 1990, 1745.
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    • The "Bosnich mechanism" was actually first proposed by Collman and Hegedus: (a) Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; p 692. For further examples, see refs 6b, 8, 23, 26, and (b) Bäckvall, J.-E.; Vågberg, J. O.; Zercher, G.; Genêt, J. P.; Denis, A. J. Org. Chem. 1987, 52, 5430. (c) Moreno-Mañas, M.; Ribas, J.; Virgili, A. J. Org. Chem. 1988, 53, 5328. (d) Kurosawa, H.; Ogoshi, S.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Chem. Lett. 1990, 1745.
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    • The "Bosnich mechanism" was actually first proposed by Collman and Hegedus: (a) Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; p 692. For further examples, see refs 6b, 8, 23, 26, and (b) Bäckvall, J.-E.; Vågberg, J. O.; Zercher, G.; Genêt, J. P.; Denis, A. J. Org. Chem. 1987, 52, 5430. (c) Moreno-Mañas, M.; Ribas, J.; Virgili, A. J. Org. Chem. 1988, 53, 5328. (d) Kurosawa, H.; Ogoshi, S.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Chem. Lett. 1990, 1745.
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    • Moreno-Mañas, M.1    Ribas, J.2    Virgili, A.3
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    • The "Bosnich mechanism" was actually first proposed by Collman and Hegedus: (a) Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; p 692. For further examples, see refs 6b, 8, 23, 26, and (b) Bäckvall, J.-E.; Vågberg, J. O.; Zercher, G.; Genêt, J. P.; Denis, A. J. Org. Chem. 1987, 52, 5430. (c) Moreno-Mañas, M.; Ribas, J.; Virgili, A. J. Org. Chem. 1988, 53, 5328. (d) Kurosawa, H.; Ogoshi, S.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Chem. Lett. 1990, 1745.
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    • Kurosawa, H.1    Ogoshi, S.2    Chatani, N.3    Kawasaki, Y.4    Murai, S.5    Ikeda, I.6
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    • note
    • 23,26 However, the reaction of 9 with malonate anion proved to be highly stereoselective (vide supra) so that this possibility can be ruled out.
  • 72
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    • note
    • 2CH, their steric effect on the ultimate environment of the double bond is, in fact, similar, as revealed by molecular modeling. Therefore, if only the steric effect of the N-substituent were taken into account, little difference in reactivity (i.e., in the reaction rate) would be anticipated for 9 and 10.
  • 73
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    • Note that this analysis lends further credence to the rejection of a similar mechanism for the cyclic series (Scheme 7).
  • 78
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    • 2O at room temperature for 2 h, is capricious and the procedure shown in the Experimental Section represents the most successful batch.
  • 80
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    • note
    • 2. However, in view of the stoichiometric nature of this reaction, it was only used in order to obtain an authentic sample of 49.
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    • This scenario parallels the occurrence of both anti-and synmechanisms for the E2 elimination reactions. For leading reviews, see: (a) Sicher, J. Angew. Chem., Int. Ed. Engl. 1972, 11, 200. (b) Sicher, J. Pure Appl. Chem. 1971, 22, 655. (c) Bartsch, R. A.; Závada, J. Chem. Rev. 1980, 80, 453.
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    • This scenario parallels the occurrence of both anti-and synmechanisms for the E2 elimination reactions. For leading reviews, see: (a) Sicher, J. Angew. Chem., Int. Ed. Engl. 1972, 11, 200. (b) Sicher, J. Pure Appl. Chem. 1971, 22, 655. (c) Bartsch, R. A.; Závada, J. Chem. Rev. 1980, 80, 453.
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    • This scenario parallels the occurrence of both anti-and synmechanisms for the E2 elimination reactions. For leading reviews, see: (a) Sicher, J. Angew. Chem., Int. Ed. Engl. 1972, 11, 200. (b) Sicher, J. Pure Appl. Chem. 1971, 22, 655. (c) Bartsch, R. A.; Závada, J. Chem. Rev. 1980, 80, 453.
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    • For a similar stereochemical switch in the cuprate-mediated allylic substitution, see: (a) Gallina, C.; Ciattini, P. G.; J. Am. Chem. Soc. 1979, 101, 1035. (b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715. (c) Tseng, C. C.; Yen, S. J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892 and refs given therein. (d) Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gómez, A. M. J. Org. Chem. 1990, 55, 2294 and refs given therein.
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    • For a similar stereochemical switch in the cuprate-mediated allylic substitution, see: (a) Gallina, C.; Ciattini, P. G.; J. Am. Chem. Soc. 1979, 101, 1035. (b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715. (c) Tseng, C. C.; Yen, S. J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892 and refs given therein. (d) Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gómez, A. M. J. Org. Chem. 1990, 55, 2294 and refs given therein.
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    • and refs given therein
    • For a similar stereochemical switch in the cuprate-mediated allylic substitution, see: (a) Gallina, C.; Ciattini, P. G.; J. Am. Chem. Soc. 1979, 101, 1035. (b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715. (c) Tseng, C. C.; Yen, S. J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892 and refs given therein. (d) Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gómez, A. M. J. Org. Chem. 1990, 55, 2294 and refs given therein.
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    • Tseng, C.C.1    Yen, S.J.2    Goering, H.L.3
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    • and refs given therein
    • For a similar stereochemical switch in the cuprate-mediated allylic substitution, see: (a) Gallina, C.; Ciattini, P. G.; J. Am. Chem. Soc. 1979, 101, 1035. (b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715. (c) Tseng, C. C.; Yen, S. J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892 and refs given therein. (d) Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gómez, A. M. J. Org. Chem. 1990, 55, 2294 and refs given therein.
    • (1990) J. Org. Chem. , vol.55 , pp. 2294
    • Valverde, S.1    Bernabé, M.2    Garcia-Ochoa, S.3    Gómez, A.M.4
  • 99
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    • note
    • 43 requires the coordinating group to be located at the carbon more distant than in the δ-position.


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