SmI2-mediated reduction of α-functionalised amides: Highly enantiospecific access to an atropisomeric amide

Synlett

Volumn , Issue 9, 1998, Pages 967-968

  Hughes, Adam D ^a   Simpkins, Nigel S ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002745259     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1838     Document Type: Article

References (18)

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2. (b) For a more recent contribution, see Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freita, L.C. G. Tetrahedron: Asymmetry 1997, 8, 3955.
3. For a listing of contributions in this area, see Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commun. 1998, 297.
4. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
5. Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T. J.Org. Chem. 1998, 63, 2634.
6. Bodansky, M. Principles of Peptide Synthesis; Springer-Verlag: New York, 1984; p 9-58.
7. 3).
8. For reviews, see (a) Molander, G. A. Org. React. 1994, 46, 211.
9. (b) Molander, G. A.; Harris, C. R. in Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A. Ed.; John Wiley and Sons: 1995; Vol 6, p 4428-4432.
10. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
11. (d) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573.
12. Fuchs, J. R.; Mitchell, M. L.; Shabangi, M.; Flowers II, R. A. Tetrahedron Lett. 1997, 38, 8157.
13. iPrOH in hexane as eluant).
14. 6) for (S)-enantiomer, see Sacha, H.; Waldmuller, D.; Braun, M. Chem. Ber. 1994, 127, 1959. Starting with 4b gave the expected enantiocomplementary results.
15. 3).
16. (b) Hirose, N.; Sohda, S.; Kuriyama, S.; Toyoshima, S. Chem. Pharm. Bull. 1973, 21, 960 (Red-Al®).
17. 2 to effect enamide saturation; the product amide having α-oxygenation survived intact, see Rigby, J. H.; Cavezza, A.; Heeg, M. J. J. Am. Chem.Soc. 1998, 120, 3664.
18. 2, freshly prepared from Sm metal (152mg, 1.01 mol) and 1,2-diiodoethane (259 mg, 0.92 mmol). After 30 min a solution of the starting amide (0.2 mmol) in THF (0.5ml) was added and the reaction mixture stirred for 24h. Standard aqueous work-up, followed by chromatography then gave the products in the yields indicated.