Zirconium-catalyzed enantioselective alkylalumination of monosubstituted alkenes proceeding via noncyclic mechanism

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1577-1578

  Kondakov, Denis Y ^a   Negishi, Ei Ichi ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; ALKENE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030001648     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953655m     Document Type: Article

References (23)

1. Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771.
2. Dzhemilev, V. M.; Vostrikova, O. S.; Sulianov, R. M. Izv. Akad. Nauk SSSR. Ser. Khim. 1983, 219.
3. Takahashi, T.; Seki, T.; Nitto, Y.; Saburi, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266.
4. For related suggestions and studies, see: (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079. (b) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (c) Lewis, D. P.; Muller, D. M.; Whitby, R. J.; Jones, R. V. H. Tetrahedron Lett. 1991, 33, 6797.
5. For related suggestions and studies, see: (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079. (b) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (c) Lewis, D. P.; Muller, D. M.; Whitby, R. J.; Jones, R. V. H. Tetrahedron Lett. 1991, 33, 6797.
6. For related suggestions and studies, see: (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079. (b) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (c) Lewis, D. P.; Muller, D. M.; Whitby, R. J.; Jones, R. V. H. Tetrahedron Lett. 1991, 33, 6797.
7. Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997.
8. Dzhemilev, V. M.; Ibragimov, A. G.; Zolotarev, A. P.; Muslukhov, R. R.; Tolstikov, G. A. Izv. Akad. Nauk SSSR. Ser. Khim. (Engl. Transl.) 1989, 194; 1991, 2570.
9. Dzhemilev, V. M.; Ibragimov, A. G.; Zolotarev, A. P.; Muslukhov, R. R.; Tolstikov, G. A. Izv. Akad. Nauk SSSR. Ser. Khim. (Engl. Transl.) 1989, 194; 1991, 2570.
10. Erker, G.; Aulbach, M.; Knickermeier, M.; Wingbermuhle, D.; Krüger, C.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590.
11. The amounts of possible dimeric products, such as 2-(n-octyl)-dodecane and 2-(n-octyl)-1-dodecene, were ≤ 1-2%, if any.
12. The absolute configurations of (R)-2-ethyl-1-hexanol (Barth, S.; Effenberger, F. Tetrahedron Assymmetry 1993, 4, 823). (R)-5-methyl-1-octanol (Sonnet, P. E.; Gazzillo, J. A.; Dudley, R. L.; Boswell, R. T. Chem. Phys. Lipids 1990, 54, 205), and (R)-5-methyl-1-heptanol (Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Synth. Commun. 1990, 20, 825) were assigned by comparing the observed optical rotation signs and magnitudes with those reported in the literature. The other assignments are more tentative and are based, in part, on empirical predictions [(a) Brewster, J. H. J. Am. Chem. Soc. 1959, 81, 5475. (b) Marker, R. E. J. Am. Chem. Soc. 1936, 58, 976)] and experimental observation of optical rotation signs and, in part, on an assumption that the uniform sign of the observed optical rotation is an indication that the face selection remains the same for all cases herein reported.
13. The absolute configurations of (R)-2-ethyl-1-hexanol (Barth, S.; Effenberger, F. Tetrahedron Assymmetry 1993, 4, 823). (R)-5-methyl-1-octanol (Sonnet, P. E.; Gazzillo, J. A.; Dudley, R. L.; Boswell, R. T. Chem. Phys. Lipids 1990, 54, 205), and (R)-5-methyl-1-heptanol (Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Synth. Commun. 1990, 20, 825) were assigned by comparing the observed optical rotation signs and magnitudes with those reported in the literature. The other assignments are more tentative and are based, in part, on empirical predictions [(a) Brewster, J. H. J. Am. Chem. Soc. 1959, 81, 5475. (b) Marker, R. E. J. Am. Chem. Soc. 1936, 58, 976)] and experimental observation of optical rotation signs and, in part, on an assumption that the uniform sign of the observed optical rotation is an indication that the face selection remains the same for all cases herein reported.
14. The absolute configurations of (R)-2-ethyl-1-hexanol (Barth, S.; Effenberger, F. Tetrahedron Assymmetry 1993, 4, 823). (R)-5-methyl-1-octanol (Sonnet, P. E.; Gazzillo, J. A.; Dudley, R. L.; Boswell, R. T. Chem. Phys. Lipids 1990, 54, 205), and (R)-5-methyl-1-heptanol (Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Synth. Commun. 1990, 20, 825) were assigned by comparing the observed optical rotation signs and magnitudes with those reported in the literature. The other assignments are more tentative and are based, in part, on empirical predictions [(a) Brewster, J. H. J. Am. Chem. Soc. 1959, 81, 5475. (b) Marker, R. E. J. Am. Chem. Soc. 1936, 58, 976)] and experimental observation of optical rotation signs and, in part, on an assumption that the uniform sign of the observed optical rotation is an indication that the face selection remains the same for all cases herein reported.
15. The absolute configurations of (R)-2-ethyl-1-hexanol (Barth, S.; Effenberger, F. Tetrahedron Assymmetry 1993, 4, 823). (R)-5-methyl-1-octanol (Sonnet, P. E.; Gazzillo, J. A.; Dudley, R. L.; Boswell, R. T. Chem. Phys. Lipids 1990, 54, 205), and (R)-5-methyl-1-heptanol (Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Synth. Commun. 1990, 20, 825) were assigned by comparing the observed optical rotation signs and magnitudes with those reported in the literature. The other assignments are more tentative and are based, in part, on empirical predictions [(a) Brewster, J. H. J. Am. Chem. Soc. 1959, 81, 5475. (b) Marker, R. E. J. Am. Chem. Soc. 1936, 58, 976)] and experimental observation of optical rotation signs and, in part, on an assumption that the uniform sign of the observed optical rotation is an indication that the face selection remains the same for all cases herein reported.
16. The absolute configurations of (R)-2-ethyl-1-hexanol (Barth, S.; Effenberger, F. Tetrahedron Assymmetry 1993, 4, 823). (R)-5-methyl-1-octanol (Sonnet, P. E.; Gazzillo, J. A.; Dudley, R. L.; Boswell, R. T. Chem. Phys. Lipids 1990, 54, 205), and (R)-5-methyl-1-heptanol (Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Synth. Commun. 1990, 20, 825) were assigned by comparing the observed optical rotation signs and magnitudes with those reported in the literature. The other assignments are more tentative and are based, in part, on empirical predictions [(a) Brewster, J. H. J. Am. Chem. Soc. 1959, 81, 5475. (b) Marker, R. E. J. Am. Chem. Soc. 1936, 58, 976)] and experimental observation of optical rotation signs and, in part, on an assumption that the uniform sign of the observed optical rotation is an indication that the face selection remains the same for all cases herein reported.
17. (a) Watson, P. L. J. Am. Chem. Soc. 1983, 105, 6491.
18. (b) Watson, P. L.; Parshell, G. W. Acc. Chem. Res. 1985, 18, 51.
19. (c) Fendrich, C. M.; Marks, T. J. J. Am. Chem. Soc. 1984, 106, 2214.
20. (d) Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bercaw, J. E. Synlett 1990, 74 and references therein.
21. Sonnet, P. E.; Gazzillo, J. A.; Dudley, R. L.; Boswell, R. T. Chem. Phys. Lipids 1990, 54, 205.
22. 2-promoted alkyl-alkene coupling, see: (a) Swanson, D. R.; Rousset, C. J.; Negishi, E.; Takahashi, T.; Seki, T.; Saburi, M.; Uchida, Y. J. Org. Chem. 1989, 54, 3521. (b) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124.
23. 2-promoted alkyl-alkene coupling, see: (a) Swanson, D. R.; Rousset, C. J.; Negishi, E.; Takahashi, T.; Seki, T.; Saburi, M.; Uchida, Y. J. Org. Chem. 1989, 54, 3521. (b) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124.