Cuprous chloride accelerated Stille reactions. A general and effective coupling system for sterically congested substrates and for enantioselective synthesis

Journal of the American Chemical Society

Volumn 121, Issue 33, 1999, Pages 7600-7605

  Han, Xiaojun ^a   Stoltz, Brian M ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; CUPROUS CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; ENANTIOMER; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033603829     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991500z     Document Type: Article

References (50)

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4. It should be noted that the stereochemistry of 1 corresponds to the anti-Felkin-Ahn product of addition of RMet to ArCH(Me)CHO. See: Reetz, M. T.; Stanchev, S.; Haning, H. Tetrahedron 1992, 48, 6813.
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6. For background on Stille coupling, including Cu(I) mediated reactions, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Org. React. 1997, 50, 1. (b) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebskind, L. S., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 5. (c) Mitchell, T. N. Synthesis 1992, 803. (d) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905. (e) Liebeskind, L. S.; Fengl, R. J. Org. Chem. 1990, 55, 5359. (f) Marino, J. P.; Long, J. K. J. Am. Chem. Soc. 1988, 110, 7916. (g) Levin, J. I. Tetrahedron Lett. 1993, 34, 6211.
7. For background on Stille coupling, including Cu(I) mediated reactions, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Org. React. 1997, 50, 1. (b) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebskind, L. S., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 5. (c) Mitchell, T. N. Synthesis 1992, 803. (d) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905. (e) Liebeskind, L. S.; Fengl, R. J. Org. Chem. 1990, 55, 5359. (f) Marino, J. P.; Long, J. K. J. Am. Chem. Soc. 1988, 110, 7916. (g) Levin, J. I. Tetrahedron Lett. 1993, 34, 6211.
8. For background on Stille coupling, including Cu(I) mediated reactions, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Org. React. 1997, 50, 1. (b) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebskind, L. S., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 5. (c) Mitchell, T. N. Synthesis 1992, 803. (d) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905. (e) Liebeskind, L. S.; Fengl, R. J. Org. Chem. 1990, 55, 5359. (f) Marino, J. P.; Long, J. K. J. Am. Chem. Soc. 1988, 110, 7916. (g) Levin, J. I. Tetrahedron Lett. 1993, 34, 6211.
9. For background on Stille coupling, including Cu(I) mediated reactions, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Org. React. 1997, 50, 1. (b) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebskind, L. S., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 5. (c) Mitchell, T. N. Synthesis 1992, 803. (d) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905. (e) Liebeskind, L. S.; Fengl, R. J. Org. Chem. 1990, 55, 5359. (f) Marino, J. P.; Long, J. K. J. Am. Chem. Soc. 1988, 110, 7916. (g) Levin, J. I. Tetrahedron Lett. 1993, 34, 6211.
10. For background on Stille coupling, including Cu(I) mediated reactions, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Org. React. 1997, 50, 1. (b) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebskind, L. S., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 5. (c) Mitchell, T. N. Synthesis 1992, 803. (d) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905. (e) Liebeskind, L. S.; Fengl, R. J. Org. Chem. 1990, 55, 5359. (f) Marino, J. P.; Long, J. K. J. Am. Chem. Soc. 1988, 110, 7916. (g) Levin, J. I. Tetrahedron Lett. 1993, 34, 6211.
11. For background on Stille coupling, including Cu(I) mediated reactions, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Org. React. 1997, 50, 1. (b) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebskind, L. S., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 5. (c) Mitchell, T. N. Synthesis 1992, 803. (d) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905. (e) Liebeskind, L. S.; Fengl, R. J. Org. Chem. 1990, 55, 5359. (f) Marino, J. P.; Long, J. K. J. Am. Chem. Soc. 1988, 110, 7916. (g) Levin, J. I. Tetrahedron Lett. 1993, 34, 6211.
12. For background on Stille coupling, including Cu(I) mediated reactions, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Org. React. 1997, 50, 1. (b) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebskind, L. S., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 5. (c) Mitchell, T. N. Synthesis 1992, 803. (d) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905. (e) Liebeskind, L. S.; Fengl, R. J. Org. Chem. 1990, 55, 5359. (f) Marino, J. P.; Long, J. K. J. Am. Chem. Soc. 1988, 110, 7916. (g) Levin, J. I. Tetrahedron Lett. 1993, 34, 6211.
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14. For example by hydrostannation using Rh-, Ni-, or Pd-catalyzed reactions or using Lipshutz's copper-mediated process. See: (a) Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065. (b) Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768. (c) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (e) Miyake, H.; Yamamura, K. Chem. Lett. 1989, 981. (f) Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619.
15. For example by hydrostannation using Rh-, Ni-, or Pd-catalyzed reactions or using Lipshutz's copper-mediated process. See: (a) Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065. (b) Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768. (c) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (e) Miyake, H.; Yamamura, K. Chem. Lett. 1989, 981. (f) Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619.
16. For example by hydrostannation using Rh-, Ni-, or Pd-catalyzed reactions or using Lipshutz's copper-mediated process. See: (a) Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065. (b) Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768. (c) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (e) Miyake, H.; Yamamura, K. Chem. Lett. 1989, 981. (f) Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619.
17. For example by hydrostannation using Rh-, Ni-, or Pd-catalyzed reactions or using Lipshutz's copper-mediated process. See: (a) Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065. (b) Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768. (c) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (e) Miyake, H.; Yamamura, K. Chem. Lett. 1989, 981. (f) Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619.
18. For example by hydrostannation using Rh-, Ni-, or Pd-catalyzed reactions or using Lipshutz's copper-mediated process. See: (a) Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065. (b) Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768. (c) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (e) Miyake, H.; Yamamura, K. Chem. Lett. 1989, 981. (f) Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619.
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