Ene Reactions of Alkynes for the Stereoselective Synthesis of Allylamines

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 1-2, 1997, Pages 143-145

  Ofial, Armin R ^b   Mayr, Herbert ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b NONE

Author keywords

Alkynes; Allylamines; Ene reactions; Enynes; Iminiumions

Indexed keywords

EID: 0030786949     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199701431     Document Type: Article

References (38)

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22. Other ene reactions of methyleneammonium ions: a) T. Cohen, A. Onopchenko, J. Org. Chem. 1983, 48, 4531-4537; b) J. H, Tidwell, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 11797-11810; A. R. Ofial, H. Mayr. J. Org. Chem. 1996, 61, 5823-5830.
23. Other ene reactions of methyleneammonium ions: a) T. Cohen, A. Onopchenko, J. Org. Chem. 1983, 48, 4531-4537; b) J. H, Tidwell, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 11797-11810; A. R. Ofial, H. Mayr. J. Org. Chem. 1996, 61, 5823-5830.
24. Other ene reactions of methyleneammonium ions: a) T. Cohen, A. Onopchenko, J. Org. Chem. 1983, 48, 4531-4537; b) J. H, Tidwell, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 11797-11810; A. R. Ofial, H. Mayr. J. Org. Chem. 1996, 61, 5823-5830.
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26. Further imino ene reactions with inverse electron demand: a) M. Novák, J. Novák, C. A. Salemink, Tetrahedron Lett. 1991, 32, 4405-4408: b) S. Laschat, M. Grehl. Angew. Chem. 1994, 106, 475-476; Angew. Chem. Int. Ed. Engl. 1994, 33, 458-461: Chem. Ber. 1994, 127, 2023-2034; S. Laschat, R. Fröhlich, B. Wibbeling, J. Org. Chem. 1996, 61, 2829-2838.
27. Further imino ene reactions with inverse electron demand: a) M. Novák, J. Novák, C. A. Salemink, Tetrahedron Lett. 1991, 32, 4405-4408: b) S. Laschat, M. Grehl. Angew. Chem. 1994, 106, 475-476; Angew. Chem. Int. Ed. Engl. 1994, 33, 458-461: Chem. Ber. 1994, 127, 2023-2034; S. Laschat, R. Fröhlich, B. Wibbeling, J. Org. Chem. 1996, 61, 2829-2838.
28. Further imino ene reactions with inverse electron demand: a) M. Novák, J. Novák, C. A. Salemink, Tetrahedron Lett. 1991, 32, 4405-4408: b) S. Laschat, M. Grehl. Angew. Chem. 1994, 106, 475-476; Angew. Chem. Int. Ed. Engl. 1994, 33, 458-461: Chem. Ber. 1994, 127, 2023-2034; S. Laschat, R. Fröhlich, B. Wibbeling, J. Org. Chem. 1996, 61, 2829-2838.
29. Further imino ene reactions with inverse electron demand: a) M. Novák, J. Novák, C. A. Salemink, Tetrahedron Lett. 1991, 32, 4405-4408: b) S. Laschat, M. Grehl. Angew. Chem. 1994, 106, 475-476; Angew. Chem. Int. Ed. Engl. 1994, 33, 458-461: Chem. Ber. 1994, 127, 2023-2034; S. Laschat, R. Fröhlich, B. Wibbeling, J. Org. Chem. 1996, 61, 2829-2838.
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36. H. Böhme, A. Sickmüller, Chem. Ber. 1977, 110, 208-216.
37. Solid alkynes were dissolved in dichloromethane prior to addilion.
38. 0.5. which can be generated in solution in analogy to the corresponding hexachloroantimonates.