Synthesis and application of macrocyclic binaphthyl ligands with extended chiral bias

Tetrahedron Asymmetry

Volumn 9, Issue 20, 1998, Pages 3607-3610

  Yan, Yuan Yong ^a   Widhalm, Michael ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; MACROCYCLIC COMPOUND; NAPHTHYL GROUP; PALLADIUM;

ALKYLATION; CHIRALITY; CYCLIZATION; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

EID: 0032561406     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00375-9     Document Type: Article

References (22)

1. (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis; VCH: Weinheim, 1993.
2. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Methods 1989; Scheffold, R., Ed.; Springer Verlag: Berlin, 1989; pp. 115.
3. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
4. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
5. (a) Widhalm, M.; Kalchhauser, H.; Kählig, H. Helv. Chim. Acta 1994, 77, 409.
6. (b) Widhalm, M.; Klintschar, G. Chem. Ber. 1994, 127, 1411.
7. (c) Wimmer, P.; Widhalm, M. Phosphorus, Sulfur Silicon 1995, 106, 105.
8. (d) Wimmer, P.; Klintschar, G.; Widhalm, M. Heterocycles 1995, 41, 2745.
9. Widhalm, M.; Wimmer, P.; Klintschar, G. J. Organomet. Chem. 1996, 523, 167.
10. Wimmer, P.; Haslinger, U.; Widhalm, M. Monatsh. Chem. in press.
11. +, 100%).
12. High asymmetric inductions have been reported for Reaction (1), cf.: Andersson, P. G.; Harden, A.; Tanner, D.; Norby, P. O. Chem. Eur. J. 1995, 1, 12; von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566; Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coates, S. W. Tetrahedron Lett. 1993, 34, 3149; Reaction (2) cf.: Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520; Reactions (3) and (4): Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089; Helmchen, G.; Kudis, S.; Sennhenn, P.; Steinhagen, H. Pure Appl. Chem. 1997, 69, 513.
13. High asymmetric inductions have been reported for Reaction (1), cf.: Andersson, P. G.; Harden, A.; Tanner, D.; Norby, P. O. Chem. Eur. J. 1995, 1, 12; von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566; Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coates, S. W. Tetrahedron Lett. 1993, 34, 3149; Reaction (2) cf.: Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520; Reactions (3) and (4): Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089; Helmchen, G.; Kudis, S.; Sennhenn, P.; Steinhagen, H. Pure Appl. Chem. 1997, 69, 513.
14. High asymmetric inductions have been reported for Reaction (1), cf.: Andersson, P. G.; Harden, A.; Tanner, D.; Norby, P. O. Chem. Eur. J. 1995, 1, 12; von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566; Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coates, S. W. Tetrahedron Lett. 1993, 34, 3149; Reaction (2) cf.: Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520; Reactions (3) and (4): Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089; Helmchen, G.; Kudis, S.; Sennhenn, P.; Steinhagen, H. Pure Appl. Chem. 1997, 69, 513.
15. High asymmetric inductions have been reported for Reaction (1), cf.: Andersson, P. G.; Harden, A.; Tanner, D.; Norby, P. O. Chem. Eur. J. 1995, 1, 12; von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566; Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coates, S. W. Tetrahedron Lett. 1993, 34, 3149; Reaction (2) cf.: Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520; Reactions (3) and (4): Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089; Helmchen, G.; Kudis, S.; Sennhenn, P.; Steinhagen, H. Pure Appl. Chem. 1997, 69, 513.
16. High asymmetric inductions have been reported for Reaction (1), cf.: Andersson, P. G.; Harden, A.; Tanner, D.; Norby, P. O. Chem. Eur. J. 1995, 1, 12; von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566; Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coates, S. W. Tetrahedron Lett. 1993, 34, 3149; Reaction (2) cf.: Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520; Reactions (3) and (4): Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089; Helmchen, G.; Kudis, S.; Sennhenn, P.; Steinhagen, H. Pure Appl. Chem. 1997, 69, 513.
17. High asymmetric inductions have been reported for Reaction (1), cf.: Andersson, P. G.; Harden, A.; Tanner, D.; Norby, P. O. Chem. Eur. J. 1995, 1, 12; von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566; Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coates, S. W. Tetrahedron Lett. 1993, 34, 3149; Reaction (2) cf.: Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520; Reactions (3) and (4): Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089; Helmchen, G.; Kudis, S.; Sennhenn, P.; Steinhagen, H. Pure Appl. Chem. 1997, 69, 513.
18. Sennhenn, P.; Gabler, B.; Helmchen, G. Tetrahedron Lett. 1994, 35, 8595.
19. Although palladium catalyzed allylic substitution reactions have been the subject of numerous mechanistic investigations the origin of enantioselection is not completely understood; different mechanistic models have been presented and arguments for both early and late transition states have been proposed for the nucleophile attack, the rate- and configuration-determining step. In this context the role of an equilibrium between preceding diastereomeric π-allyl-palladium(II) complexes was also discussed. See: Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033; Mackenzie, P. B.; Wehlan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046; Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493; see also Helmchen, G. et al. in Ref. 8.
20. Although palladium catalyzed allylic substitution reactions have been the subject of numerous mechanistic investigations the origin of enantioselection is not completely understood; different mechanistic models have been presented and arguments for both early and late transition states have been proposed for the nucleophile attack, the rate- and configuration-determining step. In this context the role of an equilibrium between preceding diastereomeric π-allyl-palladium(II) complexes was also discussed. See: Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033; Mackenzie, P. B.; Wehlan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046; Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493; see also Helmchen, G. et al. in Ref. 8.
21. Although palladium catalyzed allylic substitution reactions have been the subject of numerous mechanistic investigations the origin of enantioselection is not completely understood; different mechanistic models have been presented and arguments for both early and late transition states have been proposed for the nucleophile attack, the rate- and configuration-determining step. In this context the role of an equilibrium between preceding diastereomeric π-allyl-palladium(II) complexes was also discussed. See: Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033; Mackenzie, P. B.; Wehlan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046; Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493; see also Helmchen, G. et al. in Ref. 8.
22. Although palladium catalyzed allylic substitution reactions have been the subject of numerous mechanistic investigations the origin of enantioselection is not completely understood; different mechanistic models have been presented and arguments for both early and late transition states have been proposed for the nucleophile attack, the rate- and configuration-determining step. In this context the role of an equilibrium between preceding diastereomeric π-allyl-palladium(II) complexes was also discussed. See: Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033; Mackenzie, P. B.; Wehlan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046; Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493; see also Helmchen, G. et al. in Ref. 8.