Nickel-Catalyzed Hydroalumination of Oxabicyclic Alkenes. Ligand Effects on the Regio- and Enantioselectivity

Journal of the American Chemical Society

Volumn 117, Issue 1, 1995, Pages 532-533

  Lautens, Mark ^a   Chiu, Pauline ^a   Ma, Shihong ^a   Rovis, Tomislav ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001760103     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00106a062     Document Type: Article

References (16)

1. For a recent review of metal-catalyzed hydrosilation, see: Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 8, p 763 and references therein.
2. Metal-catalyzed hydroboration: Mannig, D.; Noth, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 878. For a review, see: Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179. For discussions on the mechanism, see: Evans, D. A.; Fu, G. C.; Anderson, B. A. J. Am. Chem. Soc. 1992, 114, 6679 and references therein.
3. Hydrostannation: (a) Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. (b) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (c) Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 1099. (e) Koerber, K.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1991, 32, 1187. (f) Casson, S.; Kocienski, P. Synthesis 1993, 1133.
4. Enantioselective hydroboration: (a) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426. (b) Sato, M.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1990, 31, 231. (c) Burgess, K.; Ohlmeyer, M. J. J. Org. Chem. 1988, 53, 5178.
5. Enantioselective hydrosilation: (a) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887. (b) Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333. (c) Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
6. For a recent review of alkene and alkyne hydroalumination, see: Eisch, J. J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 8, p 733. For seminal references, see: (a) Ziegler, K.; Holzkamp, E.; Breil, H.; Martin, H. Angew. Chem. 1955, 67, 543. (b) Eisch, J. J.; Foxton, M. W. J. Organomet. Chem. 1968, 12, 33. (c) Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1973, 12, 943. (d) Eisch, J. J.; Rhee, S.-G. J. Am. Chem. Soc. 1974, 96, 7276. (e) Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63 and ref 20.
7. Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185. (b) For an early attempt at asymmetric hydroalumination, see: Giacomelli, G.; Bertero, L.; Lardicci, L. Tetrahedron Lett. 1981, 22, 883.
8. For recent papers using oxabicyclic precursors, see: (a) Lautens, M. Synlett 1993, 177. (b) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (c) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett. 1990, 173. For studies illustrating the utility of cyclohexenols, see: Arjona, O.; de Dios, A.; Fernandez de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906.
9. For examples of the importance of functionalized cyclohexanes in organic synthesis and the approaches to prepare them, see: (a) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779. (b) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129. (c) Balci, M.; Sutbeyaz, Y.; Secen, H. Tetrahedron 1990, 46, 3715.
10. Lewis acids have been reported to accelerate the fragmentation in the product following hydroboration of 2,5-dihydrofuran, see: (a) Zweifel, G.; Plamondon, J. J. Org. Chem. 1970, 35, 898. (b) Brown, H. C.; Vara Prasad, J. V. N. J. Org. Chem. 1985, 50, 3002.
11. Unpublished work of S. Ma and A. Yee. For a related approach with a cycloheptene triol, see: Johnson, C. R.; Senanayake, C. H. J. Org. Chem. 1989, 54, 735. For a review, see: Rosen, T.; Heathcock, C. H. Tetrahedron 1986, 42, 4909.
12. Lautens, M.; Chiu, P.; Colucci, J. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 281; Angew. Chem. 1993, 105, 267.
13. For a recent discussion of the mechanism of hydrosilation, see: (a) Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151. (b) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2121.
14. For a study of relative rates of hydroalumination, see: Ziegler, K.; Gellert, H. G.; Martin, H.; Nagel, K.; Schneider, J. Justus Liebigs Ann. Chem. 1954, 589, 91.
15. Eisch, J. J.; Sexsmith, S. R.; Fichter, K. C. J. Organomet. Chem. 1990, 382, 273.
16. As measured by the Mosher method (a) Dale, J. E.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543. (b) Dale, J. E.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512] and CGC (Chiraldex G-TA, Advanced Separation Technologies Inc.). (c) The absolute stereochemistry is as indicated and was proven by comparison with an authentic sample of the enantiomer prepared by an alternative route.