Rationalization of enantioselectivities in dialkylzinc additions to benzaldehyde catalyzed by fenchone derivatives

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 77-82

  Goldfuss, Bernd ^a   Steigelmann, Melanie ^a   Khan, Saeed I ^b   Houk, K N ^b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL GROUP; BENZALDEHYDE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CRYSTAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

BENZALDEHYDES; CATALYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NORBORNANES; STEREOISOMERISM; ZINC;

EID: 0033966986     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991070v     Document Type: Article

References (44)

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11. Enantioselective diethyizinc additions to benzaldehyde: (a) Ding K.; Ishii, A.; Mikami, K. Angew. Chem. 1999, 111, 519; Angew. Chem., Int. Ed. 1999, 38, 497. (b) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. J. Org. Chem. 1998, 63, 5312. (c) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. Epoxidations: (d) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987; Angew. Chem., Int. Ed. 1999, 38, 937. Strecker reactions: (e) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. Screening: (f) Bein, T. Angew. Chem. 1999, 111, 335, Angew. Chem., Int. Ed. 1999, 38, 323. (g) Kagan, H. B. J. Organomet. Chem. 1998, 567, 3. (h) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885.
12. Enantioselective diethyizinc additions to benzaldehyde: (a) Ding K.; Ishii, A.; Mikami, K. Angew. Chem. 1999, 111, 519; Angew. Chem., Int. Ed. 1999, 38, 497. (b) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. J. Org. Chem. 1998, 63, 5312. (c) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. Epoxidations: (d) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987; Angew. Chem., Int. Ed. 1999, 38, 937. Strecker reactions: (e) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. Screening: (f) Bein, T. Angew. Chem. 1999, 111, 335, Angew. Chem., Int. Ed. 1999, 38, 323. (g) Kagan, H. B. J. Organomet. Chem. 1998, 567, 3. (h) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885.
13. Enantioselective diethyizinc additions to benzaldehyde: (a) Ding K.; Ishii, A.; Mikami, K. Angew. Chem. 1999, 111, 519; Angew. Chem., Int. Ed. 1999, 38, 497. (b) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. J. Org. Chem. 1998, 63, 5312. (c) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. Epoxidations: (d) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987; Angew. Chem., Int. Ed. 1999, 38, 937. Strecker reactions: (e) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. Screening: (f) Bein, T. Angew. Chem. 1999, 111, 335, Angew. Chem., Int. Ed. 1999, 38, 323. (g) Kagan, H. B. J. Organomet. Chem. 1998, 567, 3. (h) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885.
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15. Enantioselective diethyizinc additions to benzaldehyde: (a) Ding K.; Ishii, A.; Mikami, K. Angew. Chem. 1999, 111, 519; Angew. Chem., Int. Ed. 1999, 38, 497. (b) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. J. Org. Chem. 1998, 63, 5312. (c) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. Epoxidations: (d) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987; Angew. Chem., Int. Ed. 1999, 38, 937. Strecker reactions: (e) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. Screening: (f) Bein, T. Angew. Chem. 1999, 111, 335, Angew. Chem., Int. Ed. 1999, 38, 323. (g) Kagan, H. B. J. Organomet. Chem. 1998, 567, 3. (h) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885.
16. Enantioselective diethyizinc additions to benzaldehyde: (a) Ding K.; Ishii, A.; Mikami, K. Angew. Chem. 1999, 111, 519; Angew. Chem., Int. Ed. 1999, 38, 497. (b) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. J. Org. Chem. 1998, 63, 5312. (c) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. Epoxidations: (d) Francis, M. B.; Jacobsen, E. N. Angew. Chem. 1999, 111, 987; Angew. Chem., Int. Ed. 1999, 38, 937. Strecker reactions: (e) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. Screening: (f) Bein, T. Angew. Chem. 1999, 111, 335, Angew. Chem., Int. Ed. 1999, 38, 323. (g) Kagan, H. B. J. Organomet. Chem. 1998, 567, 3. (h) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885.
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