Indium-mediated reactions of enamines in the presence of acid

Chemistry - A European Journal

Volumn 3, Issue 7, 1997, Pages 1064-1070

  Tussa, Laurent ^a   Lebreton, Chrystèle ^a   Mosset, Paul ^a  

^a UNIV RENNES   (France)

Author keywords

Allylations; Enamines; Iminium salts; Indium; Zinc

Indexed keywords

EID: 0030842486     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030713     Document Type: Article

References (26)

1. For a review on the use of indium in synthetic chemistry, see P. Cintas, Synlett 1995, 1087-1096.
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8. CD = 19.2 Hz) respectively.
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11. Allylsilanes and allylstannanes are also known to react with iminium salts generated by the reaction of formaldehyde with amine salts to give homoallylamines: S. D. Larsen, P. A. Grieco, W. F. Fobare, J. Am. Chem. Soc. 1986, 108, 3512-3513; P. A. Grieco, W. F. Fobare, Tetrahedron Lett. 1986, 27, 5067-5070; see also E. F. Kleinman, R. A. Volkmann in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 1000-1003; A. R. Ofial, H. Mayr, J. Org. Chem. 1996, 61, 5823-5830 and ref. cited.
12. Allylsilanes and allylstannanes are also known to react with iminium salts generated by the reaction of formaldehyde with amine salts to give homoallylamines: S. D. Larsen, P. A. Grieco, W. F. Fobare, J. Am. Chem. Soc. 1986, 108, 3512-3513; P. A. Grieco, W. F. Fobare, Tetrahedron Lett. 1986, 27, 5067-5070; see also E. F. Kleinman, R. A. Volkmann in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 1000-1003; A. R. Ofial, H. Mayr, J. Org. Chem. 1996, 61, 5823-5830 and ref. cited.
13. Allylsilanes and allylstannanes are also known to react with iminium salts generated by the reaction of formaldehyde with amine salts to give homoallylamines: S. D. Larsen, P. A. Grieco, W. F. Fobare, J. Am. Chem. Soc. 1986, 108, 3512-3513; P. A. Grieco, W. F. Fobare, Tetrahedron Lett. 1986, 27, 5067-5070; see also E. F. Kleinman, R. A. Volkmann in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 1000-1003; A. R. Ofial, H. Mayr, J. Org. Chem. 1996, 61, 5823-5830 and ref. cited.
14. Allylsilanes and allylstannanes are also known to react with iminium salts generated by the reaction of formaldehyde with amine salts to give homoallylamines: S. D. Larsen, P. A. Grieco, W. F. Fobare, J. Am. Chem. Soc. 1986, 108, 3512-3513; P. A. Grieco, W. F. Fobare, Tetrahedron Lett. 1986, 27, 5067-5070; see also E. F. Kleinman, R. A. Volkmann in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 1000-1003; A. R. Ofial, H. Mayr, J. Org. Chem. 1996, 61, 5823-5830 and ref. cited.
15. For the γ-addition of allylic indium sesquihalides to hard electrophiles such as proton and carbonyl compounds, see S. Araki, T. Shimizu, P. S. Johar, S.-J. Jin, Y. Butsugan, J. Org. Chem. 1991, 56, 2538-2542.
16. S. Araki, S.-J. Jin, Y. Idou, Y. Butsugan, Bull. Chem. Soc. Jpn. 1992, 65, 1736-1738.
17. The use of indium trichloride was also reported for transmetalation reactions with allylstannanes [17] and tin [18].
18. In subsequent exploratory experiments, propargyl bromide was also shown to react with enamines in the presence of acetic acid and indium or zinc. With indium, an approximately 1:1 mixture of isomeric α-allenyl and homopropargyl tertiary amines was obtained. With zinc, the same compounds were isolated in an approximately 9:1 ratio in favor of the acetylenic amine.
19. -1 of amine) for 2 d at RT.
20. Commercial indium powder from Aldrich (99.99%, stabilized with 1% MgO), zinc powder from BDH, aluminum powder from Janssen (99%, 200 mesh), tin powder from Prolabo (carbon free, for metallurgical analyses, article no. 23713), bismuth powder from Aldrich (99.5%, 100 mesh), and indium(m) chloride from Aldrich (98%) were used.
21. S. Hünig, E. Benzing, E. Lücke, Chem. Ber. 1957, 90, 2833-2840.
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24. b) J. A. Marshall, A. W. Garofalo, ibid. 1996, 61, 8732-8738.
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