Facile synthesis of chiral isopropyl carbinols with high enantiomeric excess via catalytic enantioselective addition of diisopropylzinc to aldehydes

Tetrahedron Asymmetry

Volumn 11, Issue 14, 2000, Pages 2947-2953

  Yang, Weon Ki ^a   Cho, Byung Tae ^a  

^a Hallym University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; METHANOL DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION TIME; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 0011624478     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00253-6     Document Type: Article

References (30)

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8. 6 of n-hexyl isopropyl ketone and isobutyrophenone. From the reaction, we obtained the corresponding isopropyl carbinols having 6% ee and 21% ee, respectively.
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12. For a recent review, see: Soai, K. Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 26.1, pp. 911-922; For earlier reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856, and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, 1991; pp. 211 229; For recent works, see: (e) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974; (f) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501; (g) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, 1571-1572; (h) Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860-7867; (i) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492; (j) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1998, 63, 1364-1365.
13. For a recent review, see: Soai, K. Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 26.1, pp. 911-922; For earlier reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856, and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, 1991; pp. 211 229; For recent works, see: (e) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974; (f) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501; (g) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, 1571-1572; (h) Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860-7867; (i) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492; (j) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1998, 63, 1364-1365.
14. For a recent review, see: Soai, K. Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 26.1, pp. 911-922; For earlier reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856, and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, 1991; pp. 211 229; For recent works, see: (e) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974; (f) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501; (g) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, 1571-1572; (h) Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860-7867; (i) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492; (j) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1998, 63, 1364-1365.
15. For a recent review, see: Soai, K. Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 26.1, pp. 911-922; For earlier reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856, and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, 1991; pp. 211 229; For recent works, see: (e) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974; (f) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501; (g) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, 1571-1572; (h) Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860-7867; (i) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492; (j) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1998, 63, 1364-1365.
16. For a recent review, see: Soai, K. Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 26.1, pp. 911-922; For earlier reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856, and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, 1991; pp. 211 229; For recent works, see: (e) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974; (f) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501; (g) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, 1571-1572; (h) Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860-7867; (i) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492; (j) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1998, 63, 1364-1365.
17. For a recent review, see: Soai, K. Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 26.1, pp. 911-922; For earlier reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856, and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, 1991; pp. 211 229; For recent works, see: (e) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974; (f) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501; (g) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, 1571-1572; (h) Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860-7867; (i) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492; (j) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1998, 63, 1364-1365.
18. For a recent review, see: Soai, K. Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 26.1, pp. 911-922; For earlier reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856, and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, 1991; pp. 211 229; For recent works, see: (e) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974; (f) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501; (g) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, 1571-1572; (h) Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860-7867; (i) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492; (j) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1998, 63, 1364-1365.
19. For a recent review, see: Soai, K. Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 26.1, pp. 911-922; For earlier reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856, and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, 1991; pp. 211 229; For recent works, see: (e) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974; (f) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501; (g) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, 1571-1572; (h) Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860-7867; (i) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492; (j) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1998, 63, 1364-1365.
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