An insoluble polymer-bound phosphoramidite for the copper-catalysed enantioselective 1,4-addition of ZnEt2 to 2-cyclohexenone

Tetrahedron Asymmetry

Volumn 14, Issue 23, 2003, Pages 3647-3650

  Mandoli, Alessandro ^a   Calamante, Massimo ^a   Feringa, Ben L ^b   Salvadori, Piero ^a  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; COPPER; PHOSPHORAMIDOUS ACID; PHOSPHORUS DERIVATIVE; POLYMER; RESIN; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CROSS LINKING; ENANTIOSELECTIVITY; FILTRATION; MOLECULAR STABILITY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SOLUBILITY;

EID: 0345016372     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.004     Document Type: Article

References (27)

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2. For a summary of previous work in the field: (a) Krause, N.; Hoffman-Roder, A. Synthesis 2001, 171-196; (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236; (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; Chapter 7.
3. For a summary of previous work in the field: (a) Krause, N.; Hoffman-Roder, A. Synthesis 2001, 171-196; (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236; (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; Chapter 7.
4. For a summary of previous work in the field: (a) Krause, N.; Hoffman-Roder, A. Synthesis 2001, 171-196; (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236; (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; Chapter 7.
5. For applications of 1 in miscellaneous enantioselective transformations: (a) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705; (b) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (c) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737; (d) Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558-4559; (e) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa B. L. J. Am. Chem. Soc. 2002, 124, 14552-14553.
6. For applications of 1 in miscellaneous enantioselective transformations: (a) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705; (b) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (c) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737; (d) Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558-4559; (e) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa B. L. J. Am. Chem. Soc. 2002, 124, 14552-14553.
7. For applications of 1 in miscellaneous enantioselective transformations: (a) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705; (b) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (c) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737; (d) Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558-4559; (e) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa B. L. J. Am. Chem. Soc. 2002, 124, 14552-14553.
8. For applications of 1 in miscellaneous enantioselective transformations: (a) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705; (b) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (c) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737; (d) Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558-4559; (e) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa B. L. J. Am. Chem. Soc. 2002, 124, 14552-14553.
9. For applications of 1 in miscellaneous enantioselective transformations: (a) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705; (b) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (c) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737; (d) Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558-4559; (e) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa B. L. J. Am. Chem. Soc. 2002, 124, 14552-14553.
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16. 3, 50 MHz) 158.42, 130.43, 128.62, 128.4, 127.89, 127.77, 127.23, 114.52, 65.29, 59.50, 55.59, 55.38, 31.94, 22.94. Resonances assigned to the minor (R,S) diastereomer were present at 55.06, 54.53 and 21.84 ppm.
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20. 3, 50 MHz, aliphatic region) 72.8, 66.7, 64.9, 54.9, 54.3, 45.0-40.0 (polystyrene backbone), 29.8, 25.0.
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24. 31P NMR (THF) δ 176.2.
25. 3, 120 MHz) 144.2.
26. 6, 120 MHz) 147.1 (92%), 147.3 ppm (8%).
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