Lewis base-catalyzed addition of triethylaluminum to epoxides

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3043-3046

  Schneider, Christoph ^a   Brauner, Jörg ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Catalysis; Epoxides; Lewis bases; Triethylaluminum

Indexed keywords

ALUMINUM DERIVATIVE; ANTIMONY DERIVATIVE; ARSINE DERIVATIVE; EPOXIDE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIMERIZATION; NONHUMAN; STEREOCHEMISTRY; TEMPERATURE;

EID: 0034701471     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00332-4     Document Type: Article

References (23)

1. Reviews: (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361
2. Reviews: (b) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin-Heidelberg-New York, 1999, 3, 1309.
3. Denmark, S. E.; Barsanti, P. A.; Wong, K. T.; Stavenger, R. A. J. Org. Chem. 1998, 63, 2428.
4. For notable exceptions, see: (a) Hayashi, M.; Tamura, M.; Oguni, N. Synlett 1992, 663
5. For notable exceptions, see: (b) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668
6. For notable exceptions, see: (c) Oguni, N.; Miyagi, Y.; Itoh, K. Tetrahedron Lett. 1998, 39, 9023
7. For notable exceptions, see: (d) Ooi, T.; Kagoshima, N.; Ichigawa, H.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 3328
8. For notable exceptions, using stoichiometric amounts of activating agents, see: (e) Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron: Asymmetry 1996, 7, 2483
9. For notable exceptions, using stoichiometric amounts of activating agents, see: (f) Alexakis, A.; Vrancken, E.; Mangeney, P. Synlett 1998, 1165
10. For notable exceptions, using stoichiometric amounts of activating agents, see: (g) Abe, N.; Hanawa, H.; Maruoka, K.; Sasaki, M.; Miyashita, M. Tetrahedron Lett. 1999, 40, 5369.
11. (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071
12. (b) Soai, K.; Watanabe, M.; Koyano, M. Bull. Chem. Soc. Jpn. 1989, 62, 2124.
13. 4 and evaporated in vacuo. The yields given in Table 1 were determined by GC against n-decane as internal standard. For preparative purposes the crude product was purified by chromatography over silica gel (ether:pentane 1:1) to yield 116 mg (91%) of trans-2-ethyl-1-cyclohexanol (3). The structure of the products 3-5 was determined by NMR, IR, UV, MS in comparison to the published data, for compound 3 see: (a) Bryan Jones, J.; Takemura, T. Can. J. Chem. 1982, 60, 2950
14. 4 and evaporated in vacuo. The yields given in Table 1 were determined by GC against n-decane as internal standard. For preparative purposes the crude product was purified by chromatography over silica gel (ether:pentane 1:1) to yield 116 mg (91%) of trans-2-ethyl-1-cyclohexanol (3). The structure of the products 3-5 was determined by NMR, IR, UV, MS in comparison to the published data, for compound 4 see: (b) Berrada, S.; Desert, S.; Metzner, P. Tetrahedron 1988, 44, 3575
15. 4 and evaporated in vacuo. The yields given in Table 1 were determined by GC against n-decane as internal standard. For preparative purposes the crude product was purified by chromatography over silica gel (ether:pentane 1:1) to yield 116 mg (91%) of trans-2-ethyl-1-cyclohexanol (3). The structure of the products 3-5 was determined by NMR, IR, UV, MS in comparison to the published data, for compound 5 see: (c) Guijarro, D.; Guillena, G.; Mancheno, B.; Yus, M. Tetrahedron 1994, 50, 3427.
16. Pfaltz, A.; Mattenberger, A. Angew. Chem. 1982, 94, 79; Angew. Chem., Int. Ed. Engl. 1982, 21, 71 and references cited therein.
17. Pfaltz, A.; Mattenberger, A. Angew. Chem. 1982, 94, 79; Angew. Chem., Int. Ed. Engl. 1982, 21, 71 and references cited therein.
18. 31P NMR studies, see: (a) Benn, R.; Rufinska, A.; Lehmkul, H.; Janssen, E.; Krüger, C. Angew. Chem. 1983, 95, 808; Angew. Chem., Int. Ed. Engl. 1983, 22, 779
19. 31P NMR studies, see: (b) Barron, A. R. J. Chem. Soc., Dalton Trans. 1988, 3047.
20. Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537.
21. Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103.
22. For catalytic enantioselective addition reactions of trialkylaluminums to aldehydes, see: (a) Chan, A. S. C.; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080
23. For catalytic enantioselective addition reactions of trialkylaluminums to aldehydes, see: (b) Pagenkopf, B. L.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 9593.