Cerium(III)-catalyzed addition of diethylzinc to carbonyl compounds

Synlett

Volumn , Issue 11, 2002, Pages 1922-1924

  Fischer, Stefan ^a   Groth, Ulrich ^a   Jeske, Mario ^b   Schütz, Thorben ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b BAYER AG   (Germany)

Author keywords

Addition to carbonyls; Catalysis; Cerium; Diethylzinc; Lanthanides

Indexed keywords

ALDEHYDE; ALIPHATIC KETONE; CARBONYL DERIVATIVE; CERIUM; DIETHYLZINC; LANTHANIDE; REAGENT; SCAVENGER; TETRAHYDROFURAN;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 0036418967     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34897     Document Type: Article

References (29)

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11. Lewis bases: (a) Langer, F.; Schwinjk, L.; Devasagayaraj, A.; Chavant, P.-V.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (b) Kitamura, M.; Oka, H.; Noyori, R. Terrahedron 1999, 55, 3605. (c) Soai, K.; Yokoyama, S.; Ebihara, K J. Chem. Soc., Chem. Commun. 1987, 1690. (d) Rosini, C.; Franzini, L.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1990, 1, 587. (e) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207. (f) Huang, W.; Hu, Q.; Pu, L. J. Org. Chem. 1998, 63, 1364, (g) Cobb, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (h) Nevalainen, M.; Nevalainen, V. Tetrahedron: Asymmetry 2001, 12, 1771. (i) Liu, D.-X.; Zhang, L.-C.; Wang Q.; Da, C.-S.; Xin, Z.-Q.; Wang, R.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2001, 3, 2733. (j) Schinnerl, M.; Seitz, M.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259.
12. Lewis bases: (a) Langer, F.; Schwinjk, L.; Devasagayaraj, A.; Chavant, P.-V.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (b) Kitamura, M.; Oka, H.; Noyori, R. Terrahedron 1999, 55, 3605. (c) Soai, K.; Yokoyama, S.; Ebihara, K J. Chem. Soc., Chem. Commun. 1987, 1690. (d) Rosini, C.; Franzini, L.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1990, 1, 587. (e) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207. (f) Huang, W.; Hu, Q.; Pu, L. J. Org. Chem. 1998, 63, 1364, (g) Cobb, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (h) Nevalainen, M.; Nevalainen, V. Tetrahedron: Asymmetry 2001, 12, 1771. (i) Liu, D.-X.; Zhang, L.-C.; Wang Q.; Da, C.-S.; Xin, Z.-Q.; Wang, R.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2001, 3, 2733. (j) Schinnerl, M.; Seitz, M.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259.
13. Lewis bases: (a) Langer, F.; Schwinjk, L.; Devasagayaraj, A.; Chavant, P.-V.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (b) Kitamura, M.; Oka, H.; Noyori, R. Terrahedron 1999, 55, 3605. (c) Soai, K.; Yokoyama, S.; Ebihara, K J. Chem. Soc., Chem. Commun. 1987, 1690. (d) Rosini, C.; Franzini, L.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1990, 1, 587. (e) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207. (f) Huang, W.; Hu, Q.; Pu, L. J. Org. Chem. 1998, 63, 1364, (g) Cobb, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (h) Nevalainen, M.; Nevalainen, V. Tetrahedron: Asymmetry 2001, 12, 1771. (i) Liu, D.-X.; Zhang, L.-C.; Wang Q.; Da, C.-S.; Xin, Z.-Q.; Wang, R.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2001, 3, 2733. (j) Schinnerl, M.; Seitz, M.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259.
14. Lewis bases: (a) Langer, F.; Schwinjk, L.; Devasagayaraj, A.; Chavant, P.-V.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (b) Kitamura, M.; Oka, H.; Noyori, R. Terrahedron 1999, 55, 3605. (c) Soai, K.; Yokoyama, S.; Ebihara, K J. Chem. Soc., Chem. Commun. 1987, 1690. (d) Rosini, C.; Franzini, L.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1990, 1, 587. (e) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207. (f) Huang, W.; Hu, Q.; Pu, L. J. Org. Chem. 1998, 63, 1364, (g) Cobb, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (h) Nevalainen, M.; Nevalainen, V. Tetrahedron: Asymmetry 2001, 12, 1771. (i) Liu, D.-X.; Zhang, L.-C.; Wang Q.; Da, C.-S.; Xin, Z.-Q.; Wang, R.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2001, 3, 2733. (j) Schinnerl, M.; Seitz, M.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259.
15. Lewis bases: (a) Langer, F.; Schwinjk, L.; Devasagayaraj, A.; Chavant, P.-V.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (b) Kitamura, M.; Oka, H.; Noyori, R. Terrahedron 1999, 55, 3605. (c) Soai, K.; Yokoyama, S.; Ebihara, K J. Chem. Soc., Chem. Commun. 1987, 1690. (d) Rosini, C.; Franzini, L.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1990, 1, 587. (e) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207. (f) Huang, W.; Hu, Q.; Pu, L. J. Org. Chem. 1998, 63, 1364, (g) Cobb, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (h) Nevalainen, M.; Nevalainen, V. Tetrahedron: Asymmetry 2001, 12, 1771. (i) Liu, D.-X.; Zhang, L.-C.; Wang Q.; Da, C.-S.; Xin, Z.-Q.; Wang, R.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2001, 3, 2733. (j) Schinnerl, M.; Seitz, M.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259.
16. Lewis bases: (a) Langer, F.; Schwinjk, L.; Devasagayaraj, A.; Chavant, P.-V.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (b) Kitamura, M.; Oka, H.; Noyori, R. Terrahedron 1999, 55, 3605. (c) Soai, K.; Yokoyama, S.; Ebihara, K J. Chem. Soc., Chem. Commun. 1987, 1690. (d) Rosini, C.; Franzini, L.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1990, 1, 587. (e) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207. (f) Huang, W.; Hu, Q.; Pu, L. J. Org. Chem. 1998, 63, 1364, (g) Cobb, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (h) Nevalainen, M.; Nevalainen, V. Tetrahedron: Asymmetry 2001, 12, 1771. (i) Liu, D.-X.; Zhang, L.-C.; Wang Q.; Da, C.-S.; Xin, Z.-Q.; Wang, R.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2001, 3, 2733. (j) Schinnerl, M.; Seitz, M.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259.
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29. 4) organic layers were then liberated from the solvent and purified by flash chromatography eluting with EtOAc/petroleum ether.