Enantioselective Synthesis of 1-Ferrocenylalkylamines via 1,2-Addition of Organolithium Compounds to Ferrocenecarboxaldehyde-SAMP-Hydrazone

Synlett

Volumn 1996, Issue 2, 1996, Pages 126-128

  Enders, Dieter ^a   Lochtman, René ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842539585     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5345     Document Type: Article

References (51)

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32. Enders, D. in Selectivity - A Goal for Synthetic Efficiency; Bartmann, W.; Trost, B.M., Eds.; Verlag Chemie: Weinheim, 1984; p. 65. Enders, D. in Current Trends in Organic Synthesis, Nozaki, H., Ed.; Pergamon Press: Oxford, 1983; p. 151. Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. Enders, D.; Reinhold, U. Angew. Chem. 1995, 107, 1332; Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Enders, D.; Schankat, J.; Klatt, M. Synlett 1994, 795. Enders, D.; Funk, R.; Klatt, M.; Raabe, G.; Hovestreydt, E.R. Angew. Chem. 1993, 105, 418; Angew. Chem. Int. Ed. Engl. 1993, 32, 418. Enders, D.; Tiebes, J. Liebigs Ann. Chem. 1993, 173. Enders, D.; Klatt, M.; Funk, R. Synlett 1993, 226. Enders, D.; Bartzen, D. Liebigs Ann. Chem. 1991, 569. Enders, D.; Schubert, H.; Nübling, C. Angew. Chem. 1986, 98, 1118; Angew. Chem. Int. Ed. Engl. 1986, 25, 1109. Enders, D.; Schubert, H. Angew. Chem. 1984, 96, 368; Angew. Chem. Int. Ed. Engl. 1984, 23, 365.
33. Enders, D. in Selectivity - A Goal for Synthetic Efficiency; Bartmann, W.; Trost, B.M., Eds.; Verlag Chemie: Weinheim, 1984; p. 65. Enders, D. in Current Trends in Organic Synthesis, Nozaki, H., Ed.; Pergamon Press: Oxford, 1983; p. 151. Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. Enders, D.; Reinhold, U. Angew. Chem. 1995, 107, 1332; Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Enders, D.; Schankat, J.; Klatt, M. Synlett 1994, 795. Enders, D.; Funk, R.; Klatt, M.; Raabe, G.; Hovestreydt, E.R. Angew. Chem. 1993, 105, 418; Angew. Chem. Int. Ed. Engl. 1993, 32, 418. Enders, D.; Tiebes, J. Liebigs Ann. Chem. 1993, 173. Enders, D.; Klatt, M.; Funk, R. Synlett 1993, 226. Enders, D.; Bartzen, D. Liebigs Ann. Chem. 1991, 569. Enders, D.; Schubert, H.; Nübling, C. Angew. Chem. 1986, 98, 1118; Angew. Chem. Int. Ed. Engl. 1986, 25, 1109. Enders, D.; Schubert, H. Angew. Chem. 1984, 96, 368; Angew. Chem. Int. Ed. Engl. 1984, 23, 365.
34. Enders, D. in Selectivity - A Goal for Synthetic Efficiency; Bartmann, W.; Trost, B.M., Eds.; Verlag Chemie: Weinheim, 1984; p. 65. Enders, D. in Current Trends in Organic Synthesis, Nozaki, H., Ed.; Pergamon Press: Oxford, 1983; p. 151. Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. Enders, D.; Reinhold, U. Angew. Chem. 1995, 107, 1332; Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Enders, D.; Schankat, J.; Klatt, M. Synlett 1994, 795. Enders, D.; Funk, R.; Klatt, M.; Raabe, G.; Hovestreydt, E.R. Angew. Chem. 1993, 105, 418; Angew. Chem. Int. Ed. Engl. 1993, 32, 418. Enders, D.; Tiebes, J. Liebigs Ann. Chem. 1993, 173. Enders, D.; Klatt, M.; Funk, R. Synlett 1993, 226. Enders, D.; Bartzen, D. Liebigs Ann. Chem. 1991, 569. Enders, D.; Schubert, H.; Nübling, C. Angew. Chem. 1986, 98, 1118; Angew. Chem. Int. Ed. Engl. 1986, 25, 1109. Enders, D.; Schubert, H. Angew. Chem. 1984, 96, 368; Angew. Chem. Int. Ed. Engl. 1984, 23, 365.
35. Enders, D. in Selectivity - A Goal for Synthetic Efficiency; Bartmann, W.; Trost, B.M., Eds.; Verlag Chemie: Weinheim, 1984; p. 65. Enders, D. in Current Trends in Organic Synthesis, Nozaki, H., Ed.; Pergamon Press: Oxford, 1983; p. 151. Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970. Enders, D.; Reinhold, U. Angew. Chem. 1995, 107, 1332; Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Enders, D.; Schankat, J.; Klatt, M. Synlett 1994, 795. Enders, D.; Funk, R.; Klatt, M.; Raabe, G.; Hovestreydt, E.R. Angew. Chem. 1993, 105, 418; Angew. Chem. Int. Ed. Engl. 1993, 32, 418. Enders, D.; Tiebes, J. Liebigs Ann. Chem. 1993, 173. Enders, D.; Klatt, M.; Funk, R. Synlett 1993, 226. Enders, D.; Bartzen, D. Liebigs Ann. Chem. 1991, 569. Enders, D.; Schubert, H.; Nübling, C. Angew. Chem. 1986, 98, 1118; Angew. Chem. Int. Ed. Engl. 1986, 25, 1109. Enders, D.; Schubert, H. Angew. Chem. 1984, 96, 368; Angew. Chem. Int. Ed. Engl. 1984, 23, 365.
36. Enders, D.; Klatt, M. in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A., Ed.; Wiley: New York, 1995, in press. Enders, D. in Asymmetric Synthesis; Vol. 3; Morrison, J.D., Ed.; Academic Press: Orlando, 1984; p. 275. Enders, D.; Fey, P.; Kipphardt, H. Org. Synth. 1987, 65, 183. Enders, D.; Fey, P.; Kipphardt, H. Org. Prep. Proced. Int. 1985, 17, 1.
37. Enders, D.; Klatt, M. in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A., Ed.; Wiley: New York, 1995, in press. Enders, D. in Asymmetric Synthesis; Vol. 3; Morrison, J.D., Ed.; Academic Press: Orlando, 1984; p. 275. Enders, D.; Fey, P.; Kipphardt, H. Org. Synth. 1987, 65, 183. Enders, D.; Fey, P.; Kipphardt, H. Org. Prep. Proced. Int. 1985, 17, 1.
38. Enders, D.; Klatt, M. in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A., Ed.; Wiley: New York, 1995, in press. Enders, D. in Asymmetric Synthesis; Vol. 3; Morrison, J.D., Ed.; Academic Press: Orlando, 1984; p. 275. Enders, D.; Fey, P.; Kipphardt, H. Org. Synth. 1987, 65, 183. Enders, D.; Fey, P.; Kipphardt, H. Org. Prep. Proced. Int. 1985, 17, 1.
39. Enders, D.; Klatt, M. in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A., Ed.; Wiley: New York, 1995, in press. Enders, D. in Asymmetric Synthesis; Vol. 3; Morrison, J.D., Ed.; Academic Press: Orlando, 1984; p. 275. Enders, D.; Fey, P.; Kipphardt, H. Org. Synth. 1987, 65, 183. Enders, D.; Fey, P.; Kipphardt, H. Org. Prep. Proced. Int. 1985, 17, 1.
40. Details of the X-ray structure analysis of (S)-2 may be obtained through the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344, Eggenstein-Leopoldshafen, Germany, upon quoting the deposi-tory number CSD-59185, the authors and the bibliographical data.
41. Bailey, W.F.; Punzalan, E.R., J. Org. Chem. 1990, 55, 5404.
42. Funk, R. Dissertation RWTH Aachen, 1990. Dale, J.A.; Mosher, H.S. J. Am. Chem. Soc. 1973, 95, 512. Dale, J.A.; Mosher, H.S. J. Org. Chem. 1969, 34, 2543.
43. Funk, R. Dissertation RWTH Aachen, 1990. Dale, J.A.; Mosher, H.S. J. Am. Chem. Soc. 1973, 95, 512. Dale, J.A.; Mosher, H.S. J. Org. Chem. 1969, 34, 2543.
44. Funk, R. Dissertation RWTH Aachen, 1990. Dale, J.A.; Mosher, H.S. J. Am. Chem. Soc. 1973, 95, 512. Dale, J.A.; Mosher, H.S. J. Org. Chem. 1969, 34, 2543.
45. Schubert, H. Dissertation Universität Bonn, 1985.
46. Details of the X-ray structure analysis of (S,R)-3d may be obtained through the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344, Eggenstein-Leopoldshafen, Germany, upon quoting the depository number CSD-59185, the authors and the bibliographical data.
47. 2O: C 62.59; H 6.80; N 8.59. Found: C 62.54; H 6.92; N 8.43.
48. 4 and concentrated in vacuo. The air sensitive hydrazines (S,R)-3 were used without futher purification.
49. 2, petroleum ether/ethyl acetate 1/1).
50. d) Preparation of Raney nickel: Ni/Al (8g/mmol) was suspended in 100 mL water and treated cautiously with sodium hydroxide until hydrogen evolution ceased. The suspension was heated to 80°C for 1h. The black solid was washed with water (20 × 30 mL), 1% aqueous formic acid (3 × 30 mL), water (3 × 30 mL) and methanol (3 × 30 mL). Afterwards the resultant Raney nickel was dried for 6h in vacuo and suspended carefully in dry methanol under argon.
51. 13C-NMR, IR, MS, and elemental analyses).