A multicomponent redox system accounts for the first Nozaki-Hiyama-Kishi reactions catalytic in chromium

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2533-2534

  Fürstner, Alois ^a   Shi, Nongyuan ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; CHROMIUM DERIVATIVE; ORGANIC COMPOUND;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029990032     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9537538     Document Type: Article

References (41)

1. (a) Okude. Y.; Hirano. S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179-3181.
2. (b) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 5281-5284.
3. (c) Hiyama, T.; Kimura, K.; Nozaki, H. Tetrahedron Lett. 1981, 1037-1040.
4. (d) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 5585-5588.
5. Reviews: (a) Saccomano, N. A. In Comprehesive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 173-209. (b) Cintas, P. Synthesis 1992, 248-257. (c) Hodgson, D. M. J. Organomet. Chem. 1994, 476, 1-5.
6. Reviews: (a) Saccomano, N. A. In Comprehesive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 173-209. (b) Cintas, P. Synthesis 1992, 248-257. (c) Hodgson, D. M. J. Organomet. Chem. 1994, 476, 1-5.
7. Reviews: (a) Saccomano, N. A. In Comprehesive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 173-209. (b) Cintas, P. Synthesis 1992, 248-257. (c) Hodgson, D. M. J. Organomet. Chem. 1994, 476, 1-5.
8. For the use of substrates other than halides, see the following, (a) Alkenyltriflates: Takai, K.; Tagashira, M.; Kuroda, T.; Oshima. K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048-6050. (b) Allylic phosphates: Nowotny, S.; Tucker, C. E.; Jubert. C.; Knochel, P. J. Org. Chem. 1995, 60, 2762-2772.
9. For the use of substrates other than halides, see the following, (a) Alkenyltriflates: Takai, K.; Tagashira, M.; Kuroda, T.; Oshima. K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048-6050. (b) Allylic phosphates: Nowotny, S.; Tucker, C. E.; Jubert. C.; Knochel, P. J. Org. Chem. 1995, 60, 2762-2772.
10. (a) Jin, H.: Uenishi. J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644-5646.
11. (b) Kishi, Y. Pure Appl. Chem. 1992, 64, 343-350. This nickel effect has been independently reported by Nozaki et al., cf. ref 3a.
12. Stereoselective reactions of crotylchromium species have received particular attention, cf.: (a) Mulzer, J.; Kattner, L.; Strecker, A. R.: Schröder, C.; Buschmann, J.: Lehmann, C.; Luger, P. J. Am. Chem. Soc. 1991, 113, 4218-4229. (b) Jubert, C.; Nowotny, S.; Komemann. D.; Antes, L; Tucker, C. E.; Knochel, P. J. Org. Chem. 1992, 57, 6384-6386. (c) Takai, K.; Nitta, K.; Utimoto, K. Tetrahedron Lett. 1988, 5263-5266. (d) Buse. C. T.; Heathcock, C. H. Tetrahedron Lett. 1978, 1685-1688. (e) Lewis. M. D.; Kishi, Y. Tetrahedron Lett. 1982, 2343-2346.
13. Stereoselective reactions of crotylchromium species have received particular attention, cf.: (a) Mulzer, J.; Kattner, L.; Strecker, A. R.: Schröder, C.; Buschmann, J.: Lehmann, C.; Luger, P. J. Am. Chem. Soc. 1991, 113, 4218-4229. (b) Jubert, C.; Nowotny, S.; Komemann. D.; Antes, L; Tucker, C. E.; Knochel, P. J. Org. Chem. 1992, 57, 6384-6386. (c) Takai, K.; Nitta, K.; Utimoto, K. Tetrahedron Lett. 1988, 5263-5266. (d) Buse. C. T.; Heathcock, C. H. Tetrahedron Lett. 1978, 1685-1688. (e) Lewis. M. D.; Kishi, Y. Tetrahedron Lett. 1982, 2343-2346.
14. Stereoselective reactions of crotylchromium species have received particular attention, cf.: (a) Mulzer, J.; Kattner, L.; Strecker, A. R.: Schröder, C.; Buschmann, J.: Lehmann, C.; Luger, P. J. Am. Chem. Soc. 1991, 113, 4218-4229. (b) Jubert, C.; Nowotny, S.; Komemann. D.; Antes, L; Tucker, C. E.; Knochel, P. J. Org. Chem. 1992, 57, 6384-6386. (c) Takai, K.; Nitta, K.; Utimoto, K. Tetrahedron Lett. 1988, 5263-5266. (d) Buse. C. T.; Heathcock, C. H. Tetrahedron Lett. 1978, 1685-1688. (e) Lewis. M. D.; Kishi, Y. Tetrahedron Lett. 1982, 2343-2346.
15. Stereoselective reactions of crotylchromium species have received particular attention, cf.: (a) Mulzer, J.; Kattner, L.; Strecker, A. R.: Schröder, C.; Buschmann, J.: Lehmann, C.; Luger, P. J. Am. Chem. Soc. 1991, 113, 4218-4229. (b) Jubert, C.; Nowotny, S.; Komemann. D.; Antes, L; Tucker, C. E.; Knochel, P. J. Org. Chem. 1992, 57, 6384-6386. (c) Takai, K.; Nitta, K.; Utimoto, K. Tetrahedron Lett. 1988, 5263-5266. (d) Buse. C. T.; Heathcock, C. H. Tetrahedron Lett. 1978, 1685-1688. (e) Lewis. M. D.; Kishi, Y. Tetrahedron Lett. 1982, 2343-2346.
16. Stereoselective reactions of crotylchromium species have received particular attention, cf.: (a) Mulzer, J.; Kattner, L.; Strecker, A. R.: Schröder, C.; Buschmann, J.: Lehmann, C.; Luger, P. J. Am. Chem. Soc. 1991, 113, 4218-4229. (b) Jubert, C.; Nowotny, S.; Komemann. D.; Antes, L; Tucker, C. E.; Knochel, P. J. Org. Chem. 1992, 57, 6384-6386. (c) Takai, K.; Nitta, K.; Utimoto, K. Tetrahedron Lett. 1988, 5263-5266. (d) Buse. C. T.; Heathcock, C. H. Tetrahedron Lett. 1978, 1685-1688. (e) Lewis. M. D.; Kishi, Y. Tetrahedron Lett. 1982, 2343-2346.
17. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
18. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
19. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
20. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
21. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
22. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
23. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
24. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
25. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
26. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
27. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
28. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
29. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
30. See: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato. M.; Untersteller, E.; Xiao, X. Y. J. Am. Chem. Soc. 1995, 117, 1171-1172. (b) Kishi. Y. Chemtracts: Org. Chem. 1988. 1, 253-265. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.: Jung. S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164. (d) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (e) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200. (f) Chen, S. H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.: Danishefsky, S. J. J. Org. Chem. 1991, 50, 5834-5845. (g) White, J. D.: Jensen, M. S. J. Am. Chem. Soc. 1995. 117, 6224-6233. (h) Lu. Y. F.; Hartwig, C. W.; Fallis. A. G. J. Org. Chem. 1993, 58, 4202-4204. (i) Still, C. W.; Mobilio, D. J. Org. Chem. 1983, 48, 4785-4786. (j) Eckhardt, M.: Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 5167-5170. (k) Dancy, I.: Skrydstrup, T.: Crévisy, C.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1995, 799-800. (l) Brandstetter, T.; Maier, M. E. Tetrahedron 1994, 50, 1435-1448. (m) Paquette, L. A.: Astles, P. C. J. Org. Chem. 1993, 58, 165-169. (n) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
31. Chen, C.: Tagami, K.: Kishi, Y. J. Org. Chem. 1995, 60, 5386-5387.
32. Wuts, P. G. M.: Callen, G. R. Synth. Commun. 1986, 16, 1833-1837.
33. 3SiCl accounts for the first carbonyl coupling reactions catalytic in titanium, cf.: Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468-4475.
34. + - Mn (-1.03 V). Handbook of Chemistry and Physics. 62nd ed.; CRC Press: Boca Raton. FL. 1982.
35. (a) Cahiez, G.; Chavant, P. Y. Tetrahedron Len. 1989, 7373-7376.
36. (b) Hiyama, T.: Sawahata. M.; Obayashi. M. Chem. Lett. 1983, 1237-1238.
37. Complete silylation could not be reached. This seems to be a limiting factor for the number of turnovers.
38. 2 should be colorless: pale-green batches result in lower yields.
39. A representative procedure is described in the supporting information.
40. Fürstner, A.: Csuk. R.; Rohrer, C.: Weidmann, H. J. Chem. Soc., Perkin Trans. I 1988, 1729-1734 and literature cited therein.
41. 2 catalyst leads to very poor conversion (19% in GC after 90 h reaction time!).