On asymmetric induction in allylic alkylation via enantiotopic facial discrimination

Journal of the American Chemical Society

Volumn 118, Issue 26, 1996, Pages 6297-6298

  Trost, Barry M ^a   Krische, Michael J ^a   Radinov, Rumen ^a   Zanoni, Giuseppe ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND;

ALKYLATION; ARTICLE; CATALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030037158     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960649x     Document Type: Article

References (39)

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2. For a few examples with the most successful ligands, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. (b) Hayashi, T.; Yamamoto, A.; Hagihara, I.; Ito, Y. Tetrahedron Lett. 1986, 27, 191. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. (d) Springz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (e) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (f) Trost, B. M.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386.
3. For a few examples with the most successful ligands, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. (b) Hayashi, T.; Yamamoto, A.; Hagihara, I.; Ito, Y. Tetrahedron Lett. 1986, 27, 191. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. (d) Springz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (e) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (f) Trost, B. M.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386.
4. For a few examples with the most successful ligands, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. (b) Hayashi, T.; Yamamoto, A.; Hagihara, I.; Ito, Y. Tetrahedron Lett. 1986, 27, 191. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. (d) Springz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (e) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (f) Trost, B. M.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386.
5. For a few examples with the most successful ligands, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. (b) Hayashi, T.; Yamamoto, A.; Hagihara, I.; Ito, Y. Tetrahedron Lett. 1986, 27, 191. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. (d) Springz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (e) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (f) Trost, B. M.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386.
6. For a few examples with the most successful ligands, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. (b) Hayashi, T.; Yamamoto, A.; Hagihara, I.; Ito, Y. Tetrahedron Lett. 1986, 27, 191. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. (d) Springz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (e) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (f) Trost, B. M.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386.
7. For a few examples with the most successful ligands, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. (b) Hayashi, T.; Yamamoto, A.; Hagihara, I.; Ito, Y. Tetrahedron Lett. 1986, 27, 191. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. (d) Springz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (e) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (f) Trost, B. M.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386.
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14. Complete or partial equilibration has normally been observed. See: (a) Hiroi, K.; Makino, K. Chem. Pharm. Bull. 1988, 36, 1744. (b) Hayashi, T.: Kishi, K.; Yamamoto, H.; Ito, Y. Tetrahedron Lett. 1990, 31, 1743. (c) Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 669. (d) Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, Y.; Uozumi, Y.; Miki, M.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 775. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3572, 3531. (f) Yamamoto, K.; Deguchi, R.; Ogimura, Y.; Tsuji, J. Chem. Lett. 1984, 1657. (g) Genét, J. P.; Grisone, S. Tetrahedron Lett. 1988, 29, 4543.
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16. Complete or partial equilibration has normally been observed. See: (a) Hiroi, K.; Makino, K. Chem. Pharm. Bull. 1988, 36, 1744. (b) Hayashi, T.: Kishi, K.; Yamamoto, H.; Ito, Y. Tetrahedron Lett. 1990, 31, 1743. (c) Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 669. (d) Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, Y.; Uozumi, Y.; Miki, M.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 775. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3572, 3531. (f) Yamamoto, K.; Deguchi, R.; Ogimura, Y.; Tsuji, J. Chem. Lett. 1984, 1657. (g) Genét, J. P.; Grisone, S. Tetrahedron Lett. 1988, 29, 4543.
17. Complete or partial equilibration has normally been observed. See: (a) Hiroi, K.; Makino, K. Chem. Pharm. Bull. 1988, 36, 1744. (b) Hayashi, T.: Kishi, K.; Yamamoto, H.; Ito, Y. Tetrahedron Lett. 1990, 31, 1743. (c) Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 669. (d) Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, Y.; Uozumi, Y.; Miki, M.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 775. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3572, 3531. (f) Yamamoto, K.; Deguchi, R.; Ogimura, Y.; Tsuji, J. Chem. Lett. 1984, 1657. (g) Genét, J. P.; Grisone, S. Tetrahedron Lett. 1988, 29, 4543.
18. Complete or partial equilibration has normally been observed. See: (a) Hiroi, K.; Makino, K. Chem. Pharm. Bull. 1988, 36, 1744. (b) Hayashi, T.: Kishi, K.; Yamamoto, H.; Ito, Y. Tetrahedron Lett. 1990, 31, 1743. (c) Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 669. (d) Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, Y.; Uozumi, Y.; Miki, M.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 775. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3572, 3531. (f) Yamamoto, K.; Deguchi, R.; Ogimura, Y.; Tsuji, J. Chem. Lett. 1984, 1657. (g) Genét, J. P.; Grisone, S. Tetrahedron Lett. 1988, 29, 4543.
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