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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 7
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Original Articles

A Route to Vicinal Diamines from the Samarium(II) Iodide-Mediated Coupling of Aldimines

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Pages 981-987 | Received 02 Jan 1990, Published online: 24 Oct 2006

References

  • Natale , N. R. 1983 . Org. Prep, and Proced. Int. , 15 : 387 For reviews on samarium diiodide-mediated reactions see, (b) Kagan, H. B. “Fundamental and Technological Aspects of Organo-f-Element Chemistry,” Marks, T. J. and Fragala, I. L.; eds., NATO ASI, Dordrecht, 1985, pp 49–76, (c) Kagan, H. B.; Sasaki, M.; Collin, J. Pure and Appl. Chem. 1988, 60, 1725; For recent applications of samarium diiodide in synthesis see: (c) Molander, G. A.; Etter, J. B. Tetrahedron Lett. 1984, 3281; (d) Molander, G. A.; Etter, J. B. J. Org. Chem. 1986, 51, 1778; (e) Molander, G. A.; Etter, J. B.; Zinke, P. W. J. Am. Chem. Soc. 1987, 109, 453;; (f) Molander, G. A.; Etter, J. B.; Synth. Commun. 1987, 17, 901; (g) Molander, G. A.; Etter, J. B. J. Am. Chem. Soc. 1987, 109, 6556; (h) Fevig, T. L.; Elliott, R. L.; Curran, D. P. J. Am. Chem. Soc. 1988, 110, 5064 and references therein; (i) Fukuzawa, S.; Iida, M.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc. Chem. Commun. 1987, 920; (j) Fukuzawa S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc. Perkin I. 1988, 1669, and references therein; (k) Molander, G. A.; Kenny, C. Tetrahedron Lett. 1987, 4367.
  • Enholm , E. J. and Trivellas , A. 1989 . J. Am. Chem. Soc. , 111 : 6463 (b) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 1063; (c) Enholm, E. J.; Satici, H.; Trivellas, A. J. Org. Chem. 1989, 54, 5841.
  • Molander , G. A. and Kenny , C. 1988 . J. Org. Chem. , 53 : 2132 (b) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236; (c) Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 765; (d) Kahn, B. E.; Rieke, R. D. Chem. Rev. 1988, 88, 733.
  • Tanaka , H. , Dhimane , H. , Fujita , H. and Ikemoto , Y. 1988 . Tetrahedron Lett. , : 3811 Other imine pinacol-like coupling reactions include, (b) Betschart, C.; Schmidt, B.; Seebach, D. Helv. Chim. Acta 1988, 71, 1999; (c) Mangeney, P.; Tejero, A.; Alexakis, A.; Grosjean, E; Normant, J. Synthesis 1988, 255, and references therein.
  • Martin , S. F. , Yang , C.-P. and Laswell , H. 1988 . Tetrahedron Lett. , : 6685 For some related chemistry of iminium ions and SmI2, see, The reduction of imines to amines with SmI2 and a proton source has been reported: Souppe, J.; Danon, J. L.; Namy, J. L.; Kagan, H. B. J. Organomet. Chem. 1983, 250, 227
  • Hollis , L. S. , Amundsen , A. R. and Stern , E. W. 1989 . J. Med. Chem. , 32 : 128 (b) Pasini, A.; Zunino, F. Angew. Chem. Int. Ed. Engl. 1987, 26, 615.
  • Kleingeld , G. C. , Nibbering , N. M. , Nico , M. M. , Halim , H. , Schwartz , H. and Wuerthwein , E. U. 1983 . Chem. Ber. , 116 : 3877 CAS reg. 88333–05–5; 109287–05–0; 109287–06–1, (b) CAS reg. 79841–85–3; Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 3811; (c) CAS reg. 62582–99–4; Shibata, K.; Saito, Y.; Yoshiyuki, U.; Katsuyoshi, M.; Matsui, M. Bull. Chem. Soc. Jpn. 1986, 59, 3323; (d) CAS. reg. 47377–65–1; Balykova, I. A.; Kozlov, N. S.; Pak, V. D. Tr. Perm. S. -kh. In-t 1975, 112, 26; (e) CAS. reg. 27845–53–0; Liebeskind, L.; Welker, M. E; Fengl, R. W. J. Am. Chem. Soc. 1986, 108, 6328.
  • Ratcliff , M. A. Jr. and Kochi , J. K. 1972 . J. Org. Chem. , 37 : 3268 CAS reg. 24431–19–4; 27549–71–9; 27549–76–4, (b) CAS reg. 119406–10–9; see ref 7(b); (c) CAS reg. 27549–72–0; 22751–69–5; 20714–67–4; Homer, L.; Skaletz, D. H. Tetrahedron Lett. 1970, 1103.

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