Highly regioselective allylic substitution mediated by chiral rhenium complexes

Organometallics

Volumn 16, Issue 9, 1997, Pages 1822-1824

  Legoupy, Stéphanie ^a   Crévisy, Christophe ^a   Guillemin, Jean Claude ^a   Grée, René ^a  

^a UNIV RENNES   (France)

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Indexed keywords

EID: 0011461296     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960853t     Document Type: Article

References (28)

1. Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds; Pergamon: New York, 1995; Chapter 8.2, pp 797-904.
2. For some examples, see the following. Palladium: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662-9670. Molybdenum: Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670-1672. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc 1990, 112, 9590-9600. Iron: Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. Enders, D.; Von Berg, S.; Jandeleit, B. Synlett 1996, 18-20.
3. For some examples, see the following. Palladium: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662-9670. Molybdenum: Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670-1672. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc 1990, 112, 9590-9600. Iron: Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. Enders, D.; Von Berg, S.; Jandeleit, B. Synlett 1996, 18-20.
4. For some examples, see the following. Palladium: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662-9670. Molybdenum: Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670-1672. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc 1990, 112, 9590-9600. Iron: Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. Enders, D.; Von Berg, S.; Jandeleit, B. Synlett 1996, 18-20.
5. For some examples, see the following. Palladium: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662-9670. Molybdenum: Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670-1672. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc 1990, 112, 9590-9600. Iron: Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. Enders, D.; Von Berg, S.; Jandeleit, B. Synlett 1996, 18-20.
6. For some examples, see the following. Palladium: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662-9670. Molybdenum: Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670-1672. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc 1990, 112, 9590-9600. Iron: Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. Enders, D.; Von Berg, S.; Jandeleit, B. Synlett 1996, 18-20.
7. For some examples, see the following. Palladium: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662-9670. Molybdenum: Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670-1672. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc 1990, 112, 9590-9600. Iron: Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. Enders, D.; Von Berg, S.; Jandeleit, B. Synlett 1996, 18-20.
8. For some examples, see the following. Palladium: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662-9670. Molybdenum: Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670-1672. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc 1990, 112, 9590-9600. Iron: Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. Enders, D.; Von Berg, S.; Jandeleit, B. Synlett 1996, 18-20.
9. Frost, C. G.; Howarth, J.; Williams, J. M., Jr. Tetrahedron: Asymmetry 1992, 3, 1089-1122. Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364 and references cited therein.
10. Frost, C. G.; Howarth, J.; Williams, J. M., Jr. Tetrahedron: Asymmetry 1992, 3, 1089-1122. Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364 and references cited therein.
11. Faller, J. W Inorg. Chem. 1980, 19, 2857-2859. Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893-3898. Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161-177.
12. Faller, J. W Inorg. Chem. 1980, 19, 2857-2859. Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893-3898. Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161-177.
13. Faller, J. W Inorg. Chem. 1980, 19, 2857-2859. Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893-3898. Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161-177.
14. Tan, W.; Lin, G. Y.; Wong, W. K.; Kiel, W. A.; Wong, V. K.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 141-152.
15. (a) Wang, Y.; Agbossou, F.; Dalton, D. M.; Liu, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2699-2713.
16. (b) Peng, T. S.; Wang, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 4535-4544.
17. (c) Johnson, T. J.; Arif, A. M.; Gladysz, J. A. Organometallics 1994, 13, 3182-3193.
18. (d) Wang, Y.; Gladysz, J. A. J. Org. Chem. 1995, 60, 903-909.
19. Legoupy, S.; Crévisy, C.; Guillemin, J.-C.; Grée, R. Tetrahedron Lett. 1996, 37, 1225-1228.
20. Batchelor, R. J.; Einstein, F. W. B.; He, Y.; Sutton, D. J. Organomet. Chem. 1994, 468, 183-191. He, Y.; Batchelor, R. J.; Einstein, F. W. B.; Sutton, D. J. Organomet. Chem. 1996, 509, 37-48. See also: Krivykh, V. V.; Gusev, O. V.; Rybinskaya, M. I. J. Organomet. Chem. 1989, 362, 351-362.
21. Batchelor, R. J.; Einstein, F. W. B.; He, Y.; Sutton, D. J. Organomet. Chem. 1994, 468, 183-191. He, Y.; Batchelor, R. J.; Einstein, F. W. B.; Sutton, D. J. Organomet. Chem. 1996, 509, 37-48. See also: Krivykh, V. V.; Gusev, O. V.; Rybinskaya, M. I. J. Organomet. Chem. 1989, 362, 351-362.
22. Batchelor, R. J.; Einstein, F. W. B.; He, Y.; Sutton, D. J. Organomet. Chem. 1994, 468, 183-191. He, Y.; Batchelor, R. J.; Einstein, F. W. B.; Sutton, D. J. Organomet. Chem. 1996, 509, 37-48. See also: Krivykh, V. V.; Gusev, O. V.; Rybinskaya, M. I. J. Organomet. Chem. 1989, 362, 351-362.
23. These reactions have been performed with racemic complexes. However, for clarity, only one enantiomer is shown in the schemes. The resolution of such rhenium complexes has been reported: Agbossou, F.; O'Connor, E. J.; Garner, C. M.; Quiros Mendez, N.; Fernandez, J. M.; Patton, A. T.; Ramsden, J. A.; Gladysz, J. A. Inorg. Synth. 1992, 29, 211-225.
24. (a) No product was obtained using phenol or allyl amine as nucleophile.
25. 1H NMR data of product 4a-c clearly show that there is no bond-shift to the sulfur atom.
26. Complex 7 can also be obtained starting from complex 1 with acetic anhydride and pyridine (yield, 71%).
27. Legoupy, S.; Crévisy, C.; Guillemin, J.-C.; Grée, R. unpublished results.
28. Casey, C. P.; Vosejpka, P. C.; Underiner, T. L.; Slough, G. A. Z.; Gavney, J. A., Jr. J. Am. Chem. Soc. 1993, 115, 6680-6688.