A first example of macromolecular Ti(IV) lewis acid in the catalytic enantioselective Mukaiyama reaction

Tetrahedron Asymmetry

Volumn 9, Issue 9, 1998, Pages 1479-1482

  Mandoli, Alessandro ^a   Pini, Dario ^a   Orlandi, Simonetta ^a   Mazzini, Francesco ^a   Salvadori, Piero ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

STYRENE; STYRENE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CHIRALITY; ENANTIOMER; MACROMOLECULE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0344074650     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00127-X     Document Type: Article

References (18)

1. Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741.
2. (a) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
3. (b) Kragi, U.; Dreisbach, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 642.
4. See for example: (a) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, O. K. Tetrahedron: Asymmetry 1995, 6, 2105. (c) Minutolo, F.; Fini, D.; Petri, A. Salvadori, P. ibid 1996, 7, 2293.
5. See for example: (a) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, O. K. Tetrahedron: Asymmetry 1995, 6, 2105. (c) Minutolo, F.; Fini, D.; Petri, A. Salvadori, P. ibid 1996, 7, 2293.
6. See for example: (a) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, O. K. Tetrahedron: Asymmetry 1995, 6, 2105. (c) Minutolo, F.; Fini, D.; Petri, A. Salvadori, P. ibid 1996, 7, 2293.
7. Blaser, H. U. Tetrahedron: Asymmetry 1991, 2, 843 and references cited therein.
8. Itsuno, S.; Kamahori, K.; Watanabe, K.; Koizumi, T.; Ito, K. Tetrahedron: Asymmetry 1994, 5, 523.
9. (a) Irrurre, J.; Fernandez-Serrat, A.; Rosanas, F. Chirality 1997, 5, 523.
10. (b) Altava, B.; Burguete, I.; Escuder, B.; Luis, S. V.; Salvador, R. V.; Fraile, J. M.; Mayoral, J.; Royo, A. J. J. Org. Chem. 1997, 62, 3126.
11. (c) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710.
12. (a) Huan, W.-S.; Hu, Q.-S.; Zheng, X.-F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313 and references therein.
13. (b) Hu, Q.-S.; Vitharana, D.; Zheng, X.-F.; Wu, C.; Kwan, C. M. S.; Pu, L. J. Org. Chem. 1996, 61, 8370.
14. For an example of an asymmetric Mukaiyama reaction with a stoichiometric amount of polymer-supported chiral borane see: Kiyooka, S.; Kido, Y.; Kaneko, Y. Tetrahedron Lett. 1994, 35, 5243.
15. Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927.
16. 3. After the usual workup, the crude material was purified by chromatography, affording 60% 3b (m.p. 70-72°C) and 75% 3c (m.p. 76-78°C), respectively.
17. 3): δ 0.2-2.8 (br. m), 3.0-3.6 (br. s), 5.0-5.4 (br. s), 6.0-7.8 (br. m), 7.8-8.2 (br. s), 12.8-13.4 (br. s).
18. iPrOH=90:10) after desilylation of 6.