Samarium diiodide-induced diastereoselective synthesis of hexahydroquinoline derivatives

Synlett

Volumn , Issue 12, 2002, Pages 2027-2030

  Gross, Steffen ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Electron transfer; Hexahydroquinolines; Ketyl; Radicals; Samarium diiodide

Indexed keywords

ANILINE DERIVATIVE; HEXAHYDROQUINOLINE DERIVATIVE; NITROGEN; PHENOL; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036458250     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35599     Document Type: Article

References (31)

1. For related phenyl-carbonyl coupling reactions, see: (a) Shiue, J.-S.; Lin, M.-H.; Fang, J.-M. J. Org. Chem. 1997, 62, 4643. (b) Kuo, Ch.-W.; Fang, J.-M. Synth. Commun. 2001, 31, 877. (c) Schmalz, H.-G.; Kiehl, O.; Gotov, B. Synlett 2002, 1253. (d) ref.(14).
2. For related phenyl-carbonyl coupling reactions, see: (a) Shiue, J.-S.; Lin, M.-H.; Fang, J.-M. J. Org. Chem. 1997, 62, 4643. (b) Kuo, Ch.-W.; Fang, J.-M. Synth. Commun. 2001, 31, 877. (c) Schmalz, H.-G.; Kiehl, O.; Gotov, B. Synlett 2002, 1253. (d) ref.(14).
3. For related phenyl-carbonyl coupling reactions, see: (a) Shiue, J.-S.; Lin, M.-H.; Fang, J.-M. J. Org. Chem. 1997, 62, 4643. (b) Kuo, Ch.-W.; Fang, J.-M. Synth. Commun. 2001, 31, 877. (c) Schmalz, H.-G.; Kiehl, O.; Gotov, B. Synlett 2002, 1253. (d) ref.(14).
4. For related phenyl-carbonyl coupling reactions, see: (a) Shiue, J.-S.; Lin, M.-H.; Fang, J.-M. J. Org. Chem. 1997, 62, 4643. (b) Kuo, Ch.-W.; Fang, J.-M. Synth. Commun. 2001, 31, 877. (c) Schmalz, H.-G.; Kiehl, O.; Gotov, B. Synlett 2002, 1253. (d) ref.(14).
5. Selected reviews on samarium diiodide promoted chemistry: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (e) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727. (f) Hölemann, A. Synlett 2001, 1497.
6. Selected reviews on samarium diiodide promoted chemistry: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (e) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727. (f) Hölemann, A. Synlett 2001, 1497.
7. Selected reviews on samarium diiodide promoted chemistry: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (e) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727. (f) Hölemann, A. Synlett 2001, 1497.
8. Selected reviews on samarium diiodide promoted chemistry: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (e) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727. (f) Hölemann, A. Synlett 2001, 1497.
9. Selected reviews on samarium diiodide promoted chemistry: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (e) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727. (f) Hölemann, A. Synlett 2001, 1497.
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22. Since samarium(II/III) species are Lewis acids one might assume a simple electrophilic substitution reaction for the formation of 2 and 4. This possibility was excluded by performing a test reaction with preformed samarium(III) iodide under the same reaction conditions but no cyclization product was observed (in the presence of HMPA as strong donor ligand the Lewis acidity of the samarium salts is effectively reduced).
23. The relative configuration was determined by NOESYNMR spectroscopy. For 17 a crystal structure was obtained to prove the relative configuration.
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26. (c) List, B.; Pojarliev, P.; Billet, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827; Basically, this Mannich reaction leads to optically active compounds with considerable enantioselectivity, but since our interest was focused on the chemo- and diastereoselectivity of the cyclization reaction the enantiomeric excess of these starting materials and the resulting products was so far not determined..
27. Basically, this Mannich reaction leads to optically active compounds with considerable enantioselectivity, but since our interest was focused on the chemo- and diastereoselectivity of the cyclization reaction the enantiomeric excess of these starting materials and the resulting products was so far not determined.
28. Brüdgam, 1.; Hartl, H. lnstitut fü Chemie, FU Berlin, 2002 unpublished results.
29. 2-induced cyclizations yields were at least equivalent to those with tertbutanol as proton source, however, so far no rule is recognizable for which substrates phenol improves the outcome. Other proton sources were also examined (including 2,6-di-tert-butylphenol or 2,2,2-trifluoroethanol) but no effect similar to that of phenol was discovered.
30. The related ortho- and meta-substituted aromatic compounds generally cyclize with considerably lower efficiency. For cyano-substituted derivatives the yields are particularly low.
31. For a recent report on related samarium diiodide induced spirocyclizations to electron-deficient aromatic compounds, see: Ohno, H.; Maeda, S.; Okumura, M.; Wakayama, R.; Tanaka, T. Chem. Commun. 2002, 316.