C2-Symmetric Copper(II) complexes as chiral lewis acids. Scope and mechanism of the catalytic enantioselective aldol additions of enolsilanes to pyruvate esters

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 686-699

  Evans, David A ^a   Burgey, Christopher S ^a   Kozlowski, Marisa C ^a   Tregay, Steven W ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; ENOLSILANE; PYRUVIC ACID DERIVATIVE; PYRUVIC ACID ESTER; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; ENANTIOMER; MOLECULAR INTERACTION; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; TEMPERATURE DEPENDENCE;

EID: 0033518571     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982983u     Document Type: Article

References (71)

1. Reference 2b, footnote 6.
2. (a) Evans, D. A.; Muny, J. A.; Kozolowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814-5815.
3. (b) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Connell, B. T. J. Am. Chem. Soc. 1999, 121, 669-685.
4. Reference 2b, footnote 7a.
5. Reference 2b, footnote 7b.
6. Representative examples: (a) Cinatrin C: Itzaki, H.; Nagashima, K.; Matsumoto, K.; Nakai, H.; Terui, Y. J. Antibiot. 1992, 45, 38-49. (b) Integerrimine: Robins, D. J. Forschr. Chem. Org. Naturst. 1982, 41, 115. (c) Harringtonine: Takano, I.; Yasuda, I.; Nishijima, M.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H. Phytochemistry 1997, 44. 735 and references therein. (d) K252a: Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem Soc. 1995, 117, 10413-10414 and references therein. (e) Fostriecin: Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753 and references therein. (f) Viridiofungin: Harris, G. H.; Jones, E. T. T.; Meinz, M. S.; Nallin-Omstead, M.; Helms, G. L.; Bills, G. F.; Zink, D.; Wilson, K. E. Tetrahedron Lett. 1993, 34, 5235-5238. (g) Erythromicin: McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M., Smith, J. W. Antibiot. Chemother. 1952, 2, 281-283. (h) Zaragozic acid: Wilson, K. E.; Burk, R. M.; Biftu, T.; Ball, R. G.; Hoogsteen, K. J. Org. Chem. 1992, 57, 7151-7158.
7. Representative examples: (a) Cinatrin C: Itzaki, H.; Nagashima, K.; Matsumoto, K.; Nakai, H.; Terui, Y. J. Antibiot. 1992, 45, 38-49. (b) Integerrimine: Robins, D. J. Forschr. Chem. Org. Naturst. 1982, 41, 115. (c) Harringtonine: Takano, I.; Yasuda, I.; Nishijima, M.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H. Phytochemistry 1997, 44. 735 and references therein. (d) K252a: Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem Soc. 1995, 117, 10413-10414 and references therein. (e) Fostriecin: Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753 and references therein. (f) Viridiofungin: Harris, G. H.; Jones, E. T. T.; Meinz, M. S.; Nallin-Omstead, M.; Helms, G. L.; Bills, G. F.; Zink, D.; Wilson, K. E. Tetrahedron Lett. 1993, 34, 5235-5238. (g) Erythromicin: McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M., Smith, J. W. Antibiot. Chemother. 1952, 2, 281-283. (h) Zaragozic acid: Wilson, K. E.; Burk, R. M.; Biftu, T.; Ball, R. G.; Hoogsteen, K. J. Org. Chem. 1992, 57, 7151-7158.
8. Representative examples: (a) Cinatrin C: Itzaki, H.; Nagashima, K.; Matsumoto, K.; Nakai, H.; Terui, Y. J. Antibiot. 1992, 45, 38-49. (b) Integerrimine: Robins, D. J. Forschr. Chem. Org. Naturst. 1982, 41, 115. (c) Harringtonine: Takano, I.; Yasuda, I.; Nishijima, M.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H. Phytochemistry 1997, 44. 735 and references therein. (d) K252a: Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem Soc. 1995, 117, 10413-10414 and references therein. (e) Fostriecin: Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753 and references therein. (f) Viridiofungin: Harris, G. H.; Jones, E. T. T.; Meinz, M. S.; Nallin-Omstead, M.; Helms, G. L.; Bills, G. F.; Zink, D.; Wilson, K. E. Tetrahedron Lett. 1993, 34, 5235-5238. (g) Erythromicin: McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M., Smith, J. W. Antibiot. Chemother. 1952, 2, 281-283. (h) Zaragozic acid: Wilson, K. E.; Burk, R. M.; Biftu, T.; Ball, R. G.; Hoogsteen, K. J. Org. Chem. 1992, 57, 7151-7158.
9. Representative examples: (a) Cinatrin C: Itzaki, H.; Nagashima, K.; Matsumoto, K.; Nakai, H.; Terui, Y. J. Antibiot. 1992, 45, 38-49. (b) Integerrimine: Robins, D. J. Forschr. Chem. Org. Naturst. 1982, 41, 115. (c) Harringtonine: Takano, I.; Yasuda, I.; Nishijima, M.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H. Phytochemistry 1997, 44. 735 and references therein. (d) K252a: Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem Soc. 1995, 117, 10413-10414 and references therein. (e) Fostriecin: Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753 and references therein. (f) Viridiofungin: Harris, G. H.; Jones, E. T. T.; Meinz, M. S.; Nallin-Omstead, M.; Helms, G. L.; Bills, G. F.; Zink, D.; Wilson, K. E. Tetrahedron Lett. 1993, 34, 5235-5238. (g) Erythromicin: McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M., Smith, J. W. Antibiot. Chemother. 1952, 2, 281-283. (h) Zaragozic acid: Wilson, K. E.; Burk, R. M.; Biftu, T.; Ball, R. G.; Hoogsteen, K. J. Org. Chem. 1992, 57, 7151-7158.
10. Representative examples: (a) Cinatrin C: Itzaki, H.; Nagashima, K.; Matsumoto, K.; Nakai, H.; Terui, Y. J. Antibiot. 1992, 45, 38-49. (b) Integerrimine: Robins, D. J. Forschr. Chem. Org. Naturst. 1982, 41, 115. (c) Harringtonine: Takano, I.; Yasuda, I.; Nishijima, M.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H. Phytochemistry 1997, 44. 735 and references therein. (d) K252a: Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem Soc. 1995, 117, 10413-10414 and references therein. (e) Fostriecin: Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753 and references therein. (f) Viridiofungin: Harris, G. H.; Jones, E. T. T.; Meinz, M. S.; Nallin-Omstead, M.; Helms, G. L.; Bills, G. F.; Zink, D.; Wilson, K. E. Tetrahedron Lett. 1993, 34, 5235-5238. (g) Erythromicin: McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M., Smith, J. W. Antibiot. Chemother. 1952, 2, 281-283. (h) Zaragozic acid: Wilson, K. E.; Burk, R. M.; Biftu, T.; Ball, R. G.; Hoogsteen, K. J. Org. Chem. 1992, 57, 7151-7158.
11. Representative examples: (a) Cinatrin C: Itzaki, H.; Nagashima, K.; Matsumoto, K.; Nakai, H.; Terui, Y. J. Antibiot. 1992, 45, 38-49. (b) Integerrimine: Robins, D. J. Forschr. Chem. Org. Naturst. 1982, 41, 115. (c) Harringtonine: Takano, I.; Yasuda, I.; Nishijima, M.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H. Phytochemistry 1997, 44. 735 and references therein. (d) K252a: Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem Soc. 1995, 117, 10413-10414 and references therein. (e) Fostriecin: Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753 and references therein. (f) Viridiofungin: Harris, G. H.; Jones, E. T. T.; Meinz, M. S.; Nallin-Omstead, M.; Helms, G. L.; Bills, G. F.; Zink, D.; Wilson, K. E. Tetrahedron Lett. 1993, 34, 5235-5238. (g) Erythromicin: McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M., Smith, J. W. Antibiot. Chemother. 1952, 2, 281-283. (h) Zaragozic acid: Wilson, K. E.; Burk, R. M.; Biftu, T.; Ball, R. G.; Hoogsteen, K. J. Org. Chem. 1992, 57, 7151-7158.
12. Representative examples: (a) Cinatrin C: Itzaki, H.; Nagashima, K.; Matsumoto, K.; Nakai, H.; Terui, Y. J. Antibiot. 1992, 45, 38-49. (b) Integerrimine: Robins, D. J. Forschr. Chem. Org. Naturst. 1982, 41, 115. (c) Harringtonine: Takano, I.; Yasuda, I.; Nishijima, M.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H. Phytochemistry 1997, 44. 735 and references therein. (d) K252a: Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem Soc. 1995, 117, 10413-10414 and references therein. (e) Fostriecin: Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753 and references therein. (f) Viridiofungin: Harris, G. H.; Jones, E. T. T.; Meinz, M. S.; Nallin-Omstead, M.; Helms, G. L.; Bills, G. F.; Zink, D.; Wilson, K. E. Tetrahedron Lett. 1993, 34, 5235-5238. (g) Erythromicin: McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M., Smith, J. W. Antibiot. Chemother. 1952, 2, 281-283. (h) Zaragozic acid: Wilson, K. E.; Burk, R. M.; Biftu, T.; Ball, R. G.; Hoogsteen, K. J. Org. Chem. 1992, 57, 7151-7158.
13. Representative examples: (a) Cinatrin C: Itzaki, H.; Nagashima, K.; Matsumoto, K.; Nakai, H.; Terui, Y. J. Antibiot. 1992, 45, 38-49. (b) Integerrimine: Robins, D. J. Forschr. Chem. Org. Naturst. 1982, 41, 115. (c) Harringtonine: Takano, I.; Yasuda, I.; Nishijima, M.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H. Phytochemistry 1997, 44. 735 and references therein. (d) K252a: Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem Soc. 1995, 117, 10413-10414 and references therein. (e) Fostriecin: Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753 and references therein. (f) Viridiofungin: Harris, G. H.; Jones, E. T. T.; Meinz, M. S.; Nallin-Omstead, M.; Helms, G. L.; Bills, G. F.; Zink, D.; Wilson, K. E. Tetrahedron Lett. 1993, 34, 5235-5238. (g) Erythromicin: McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M., Smith, J. W. Antibiot. Chemother. 1952, 2, 281-283. (h) Zaragozic acid: Wilson, K. E.; Burk, R. M.; Biftu, T.; Ball, R. G.; Hoogsteen, K. J. Org. Chem. 1992, 57, 7151-7158.
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18. Diastereoselective pyruvate aldol additions: (a) Jacobson, I. C.; Reddy, G. P. Tetrahedron Lett. 1996, 37, 8263-8266. (b) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275-276. (c) Chen, M.-Y.; Fang, J.-M. J. Chem. Soc., Perkin Trans. 1 1993, 1737-1741. (d) Ojima, I.; Yoshida, K.; Inaba, S. Chem. Lett. 1977, 429-432. Stoichtometric chiral metal-complex promoted: (e) Kobayashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629-9642. (f) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1992, 57, 1324-1326. (g) Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069-2072. One catalyzed aldol addition to pyruvate esters has been reported, but it is limited to isocyanoacetate or isocyanoacetamide nucleophiles: Ito, Y.; Sawasura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684.
19. Diastereoselective pyruvate aldol additions: (a) Jacobson, I. C.; Reddy, G. P. Tetrahedron Lett. 1996, 37, 8263-8266. (b) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275-276. (c) Chen, M.-Y.; Fang, J.-M. J. Chem. Soc., Perkin Trans. 1 1993, 1737-1741. (d) Ojima, I.; Yoshida, K.; Inaba, S. Chem. Lett. 1977, 429-432. Stoichtometric chiral metal-complex promoted: (e) Kobayashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629-9642. (f) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1992, 57, 1324-1326. (g) Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069-2072. One catalyzed aldol addition to pyruvate esters has been reported, but it is limited to isocyanoacetate or isocyanoacetamide nucleophiles: Ito, Y.; Sawasura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684.
20. Diastereoselective pyruvate aldol additions: (a) Jacobson, I. C.; Reddy, G. P. Tetrahedron Lett. 1996, 37, 8263-8266. (b) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275-276. (c) Chen, M.-Y.; Fang, J.-M. J. Chem. Soc., Perkin Trans. 1 1993, 1737-1741. (d) Ojima, I.; Yoshida, K.; Inaba, S. Chem. Lett. 1977, 429-432. Stoichtometric chiral metal-complex promoted: (e) Kobayashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629-9642. (f) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1992, 57, 1324-1326. (g) Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069-2072. One catalyzed aldol addition to pyruvate esters has been reported, but it is limited to isocyanoacetate or isocyanoacetamide nucleophiles: Ito, Y.; Sawasura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684.
21. Diastereoselective pyruvate aldol additions: (a) Jacobson, I. C.; Reddy, G. P. Tetrahedron Lett. 1996, 37, 8263-8266. (b) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275-276. (c) Chen, M.-Y.; Fang, J.-M. J. Chem. Soc., Perkin Trans. 1 1993, 1737-1741. (d) Ojima, I.; Yoshida, K.; Inaba, S. Chem. Lett. 1977, 429-432. Stoichtometric chiral metal-complex promoted: (e) Kobayashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629-9642. (f) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1992, 57, 1324-1326. (g) Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069-2072. One catalyzed aldol addition to pyruvate esters has been reported, but it is limited to isocyanoacetate or isocyanoacetamide nucleophiles: Ito, Y.; Sawasura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684.
22. Diastereoselective pyruvate aldol additions: (a) Jacobson, I. C.; Reddy, G. P. Tetrahedron Lett. 1996, 37, 8263-8266. (b) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275-276. (c) Chen, M.-Y.; Fang, J.-M. J. Chem. Soc., Perkin Trans. 1 1993, 1737-1741. (d) Ojima, I.; Yoshida, K.; Inaba, S. Chem. Lett. 1977, 429-432. Stoichtometric chiral metal-complex promoted: (e) Kobayashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629-9642. (f) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1992, 57, 1324-1326. (g) Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069-2072. One catalyzed aldol addition to pyruvate esters has been reported, but it is limited to isocyanoacetate or isocyanoacetamide nucleophiles: Ito, Y.; Sawasura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684.
23. Diastereoselective pyruvate aldol additions: (a) Jacobson, I. C.; Reddy, G. P. Tetrahedron Lett. 1996, 37, 8263-8266. (b) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275-276. (c) Chen, M.-Y.; Fang, J.-M. J. Chem. Soc., Perkin Trans. 1 1993, 1737-1741. (d) Ojima, I.; Yoshida, K.; Inaba, S. Chem. Lett. 1977, 429-432. Stoichtometric chiral metal-complex promoted: (e) Kobayashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629-9642. (f) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1992, 57, 1324-1326. (g) Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069-2072. One catalyzed aldol addition to pyruvate esters has been reported, but it is limited to isocyanoacetate or isocyanoacetamide nucleophiles: Ito, Y.; Sawasura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684.
24. Diastereoselective pyruvate aldol additions: (a) Jacobson, I. C.; Reddy, G. P. Tetrahedron Lett. 1996, 37, 8263-8266. (b) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275-276. (c) Chen, M.-Y.; Fang, J.-M. J. Chem. Soc., Perkin Trans. 1 1993, 1737-1741. (d) Ojima, I.; Yoshida, K.; Inaba, S. Chem. Lett. 1977, 429-432. Stoichtometric chiral metal-complex promoted: (e) Kobayashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629-9642. (f) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1992, 57, 1324-1326. (g) Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069-2072. One catalyzed aldol addition to pyruvate esters has been reported, but it is limited to isocyanoacetate or isocyanoacetamide nucleophiles: Ito, Y.; Sawasura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684.
25. Diastereoselective pyruvate aldol additions: (a) Jacobson, I. C.; Reddy, G. P. Tetrahedron Lett. 1996, 37, 8263-8266. (b) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275-276. (c) Chen, M.-Y.; Fang, J.-M. J. Chem. Soc., Perkin Trans. 1 1993, 1737-1741. (d) Ojima, I.; Yoshida, K.; Inaba, S. Chem. Lett. 1977, 429-432. Stoichtometric chiral metal-complex promoted: (e) Kobayashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629-9642. (f) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1992, 57, 1324-1326. (g) Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069-2072. One catalyzed aldol addition to pyruvate esters has been reported, but it is limited to isocyanoacetate or isocyanoacetamide nucleophiles: Ito, Y.; Sawasura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684.
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57. Fukuyama, T.; Lin S.-C.; Li L. J. Am. Chem. Soc. 1990, 112, 7050-7051.
58. Gennari, C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, NY, 1991; Vol. 2, Chapter 2.4.
59. Square pyramidal structures are more common than trigonal bipyramidal structures for five-coordinate Cu(II). Cambridge Structural Database survey: 51 square pyramidal structures, 9 trigonal bipyramidal structures (http://sulfur.scs.uiuc.edu/gifs/cuii.htm). See: Hathaway, B. J. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: New York, 1987; Vol. 5, Chapter 53.
60. 6), complex (ref 2b).
61. 2+ structures, the Nl-Cu-O3 bond angle was constrained during the PM3 calculations to 160°.
62. 2 complex (see Supporting Information).
63. Theoretical enantioselectivities were calculated from the results obtained experimentally at -78°C assuming that the enantioselection was only a reflection of the energy differences between two diastereomeric transition states.
64. Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515.
65. 2 catalyzed aldol reaction of (benzyloxy)acetaldehyde, see ref 2b.
66. (a) Wilcox, D. E.; Porras, A. G.; Hwang, Y. T.; Lerch, K.; Winkler, M. E.; Solomon, E. I. J. Am. Chem. Soc. 1985, 107, 4015-4027.
67. (b) Solomon. E. J.; Comments Inorg. Chem. 1984, 3, 227-320.
68. (a) Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030. The Cu(1) complexes of these ligands have also been employed as atom-transfer catalysts in aziridination and cyclopropanation reactions:
69. (b) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326-5327.
70. (c) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889-5890.
71. General information is provided in the Supporting Information.