Asymmetric synthesis of β-amino alcohols by cross-pinacol coupling of planar chiral ferrocenecarboxaldehydes with imines [2]

Journal of the American Chemical Society

Volumn 122, Issue 34, 2000, Pages 8301-8302

  Taniguchi, Nobukazu ^a   Uemura, Motokazu ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE DERIVATIVE; AMINOALCOHOL; FERROCENE; IMINE;

CHIRALITY; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034734371     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000479v     Document Type: Letter

References (26)

1. Some representative reviews: Imamoto, T. Lanthanoids in Organic Synthesis; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: London, 1994. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. Molander, G. A. Org. React. 1994, 46, 211.
2. Some representative reviews: Imamoto, T. Lanthanoids in Organic Synthesis; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: London, 1994. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. Molander, G. A. Org. React. 1994, 46, 211.
3. Some representative reviews: Imamoto, T. Lanthanoids in Organic Synthesis; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: London, 1994. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. Molander, G. A. Org. React. 1994, 46, 211.
4. Matsubara, S., Hashimoto, Y., Okano, T.; Utimoto, K. Synlett 1999, 1411-1412. Bandini, M.; Cozzi, G.; Morganti, S.; Umani-Ronchi, A. Tetrahedron Lett. 1999, 40, 1997-2000.
5. Matsubara, S., Hashimoto, Y., Okano, T.; Utimoto, K. Synlett 1999, 1411-1412. Bandini, M.; Cozzi, G.; Morganti, S.; Umani-Ronchi, A. Tetrahedron Lett. 1999, 40, 1997-2000.
6. (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 6551-6553.
7. (b) Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525-528; Shono, T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett. 1991, 2191- 2194.
8. (b) Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525- 528; Shono, T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett. 1991, 2191-2194.
9. (c) Machrouhi, Namy, J.-L. Tetrahedron Lett. 1999, 40, 1315-1318.
10. (d) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555-3556.
11. 3-catalyzed cross-coupling between aldehydes and imines. see ref 3a.
12. Reduction potential by cyclic voltammetric studies; -2.3 V for 1; -2.4 V for 2a; -2.0 V for 2c, -1.8 V for 2g.
13. The planar chiral ortho-substituted ferrocenecarboxaldehydes 6 were prepared by diastereoselective lithiation of chiral ferrocenyl acetal according to the literature procedure. Riant, O.; Samuel, O.; Flessner, T.; Taudien S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733-6745.
14. 2 in the presence of molecular selves 4 Å and catalytic amount of p-TsOH in refluxing toluene in good yields. The optical purities for imines 7 were identical with those of the corresponding aldehydes 6 by HPLC with Chiralcel OD.
15. 2 = I) and 9a with the Cambridge Crystallographic Data Centre. The X-ray data can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
16. (a) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089.
17. (b) Taniguchi, N.; Uemura Synlett 1997, 51-53.
18. (c) Taniguchi, N.; Uemura, M. Tetrahedron Lett. 1998, 39, 5385-5388.
19. (d) Taniguchi, N.; Uemura, M. Tetrahedron 1998, 54, 12775-12788.
20. Enantiomeric excess for compounds 8, 9, and 10 was determined by HPLC with Chiralcel OD.
21. The same stereochemical behavior was observed in samarium iodide-mediated cross-coupling between 2g and planar chiral benzaldehyde tricarbonylchromium complexes. N-Phenylsulfonyl benzylideneamine was also coupled with aldehydes giving β-amino alcohols.
22. Predominant anti-conformation of the C=O or C=N double bond to the ortho substituents of ferrocenyl compounds was proposed by diastereo-selective nucleophilc addition to the double bond. For a review: Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, 1995.
23. α-Ferrocenyllithium derivatives have similar stereochemical character for the electrophilic quenching depending on the α-position in the presence or absence of an ortho-substituent on the Cp ring. Ireland, T.; Perea, J. J. A.; Knochel, P. Angew, Chem. Int. Ed. 1999, 38, 1457-1460.
24. A mechanism of acyclic selection in intermolecular radical reactions and intramolecular radical cyclization between carbonyls and imines. (a) Smadja, W. Synlett 1994, 1-26. (b) Bobo, S.; Storch de Gracia, I.; Chiara, J. S. Synlett 1999, 1551-1554. (c) Boiron, A.; Zillig, P.; Faber, D.; Giese, B. J. Org. Chem. 1998, 63, 5877-5882.
25. A mechanism of acyclic selection in intermolecular radical reactions and intramolecular radical cyclization between carbonyls and imines. (a) Smadja, W. Synlett 1994, 1-26. (b) Bobo, S.; Storch de Gracia, I.; Chiara, J. S. Synlett 1999, 1551-1554. (c) Boiron, A.; Zillig, P.; Faber, D.; Giese, B. J. Org. Chem. 1998, 63, 5877-5882.
26. A mechanism of acyclic selection in intermolecular radical reactions and intramolecular radical cyclization between carbonyls and imines. (a) Smadja, W. Synlett 1994, 1-26. (b) Bobo, S.; Storch de Gracia, I.; Chiara, J. S. Synlett 1999, 1551-1554. (c) Boiron, A.; Zillig, P.; Faber, D.; Giese, B. J. Org. Chem. 1998, 63, 5877-5882.