Enantioselective addition of diethylzinc to benzaldehyde in the presence of sulfur-containing pyridine ligands

Tetrahedron Asymmetry

Volumn 9, Issue 11, 1998, Pages 1933-1940

  Chelucci, Giorgio ^a   Berta, Daniela ^a   Fabbri, Davide ^b   Pinna, Gerard A ^a   Saba, Antonio ^a   Ulgheri, Fausta ^a  

^a UNIVERSITY OF SASSARI   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

5,7 METHANE 6,6 DIMETHYL 2 PHENYL 5,6,7,8 TETRAHYDROQUINOLINE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032486292     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00167-0     Document Type: Article

References (38)

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2. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
3. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
4. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
5. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
6. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
7. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
8. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
9. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
10. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
11. 1. For a review, see: Chelucci, G. Gazz. Chim. Ital., 1992, 122, 89. Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry, 1998, 9, 407. Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem., 1997, 62, 1604. Davies. I. W.; Gerena, L.; Cai, D.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett., 1997, 38, 1145. Angell, R. M.; Barrett, A. G.; Braddock, D. C.; Swallow, S.; Vickery, B. D. J. Chem. Soc., Chem. Commun., 1997, 919. Davies, D.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun., 1997, 1351. Brunel, J. M.; Constantieux, T.; Labade, A.; Lubatti, F.; Buono, G. Tetrahedron Lett., 1997, 5971. Duboc-Toia, C.; Menage, S.; Lambeaux, C.; Fontecave, M. Tetrahedron Lett., 1997, 3727. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry, 1997, 8, 1279. Yao, S.; Johannesen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1, 1997, 2345. Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem., 1996, 8002. Datta Gupta, A.; Singh, V. Tetrahedron Lett., 1996, 37, 2633. See also Refs. 2-7.
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