Selective synthesis of functionalized allyl amines and ethers from (E)-2,3-bisphosphonated allyl bromide

Authors

  • Maha Ameur
  • Hassen Amri Professor

Abstract

An efficient and straightforward approach toward functionalized allylic amines and ethers is disclosed starting from tetraethyl (3-bromoprop-1-ene-1,2-diyl)bisphosphonate (E)-1 and secondary and tertiary amines. The coupling reaction of allyl bromide (E)-1with less bulky secondary amines provides a new family of allylamines 3, while, its reaction with more bulky secondary and tertiary amines, in methanol at reflux, led to functional allyl ethers 4 and 5.

References

- L. Aiwen, L. Xiyan, Org. Lett., 2000, 2, 2357-2360.

- (a) M. Hagithara, N. J. Anthony, T. J. Stout, J. Clardy, S. L. Schreiber, J. Am. Chem. Soc., 1992, 114, 6568- 6570; (b) S. Devadder, P. Verheyden, H. C. M. Jaspers, G. Van Binst,D. Tourué, Tetrahedron Lett., 1996, 37, 703-706.

- Y. Yamamoto, M. Schmid, J. Chem. Soc., Chem. Commun., 1989, 1310-1312.

- R. Yamaguchi, M. Moriyasu, M. Kawanisi, J. Org. Chem., 1985, 50, 287-288.

- R. M. Borzilleri, X. Zheng, R. J.Schmidt, J. A. Johnson, S. H. Kim, J. D. Marco, C. R. Fairchild, J. Z. Gougoutas, F. Y. F. Lee, B. H. Long, G. D. Vite, J. Am. Chem. Soc., 2000, 122, 8890-8897.

- S. Laschat, H. Kunz, J. Org. Chem., 1991, 56, 5883-588.

- (a) D. L. Wright, J. P. Schulte II; M. A. Page, Org. Lett., 2000, 2, 1847-1850; (b) F. X. Felpin, S. Girard, G. Vo-Thanh, R. J. Robins, J. Villiéras, J. Lebreton, J. Org. Chem., 2001, 66, 6305-6312; (c) R. P. Jain,R. M. Williams, J. Org. Chem., 2002, 67, 6361-6365; (d) R. Di Fabio, G. Alvaro, B. Bertani, D. Donati, S. Giacobbe, C. Marchioro, C. Palma, S. M. Lynn, J. Org. Chem., 2002, 67, 7319-7328; (e) P. V. Ramachandran, T. E. Burghardt, L.Bland-Berry, J. Org. Chem., 2005, 70, 7911-7918; (g) P. Besada, L. Mamedova, C. J. Thomas, S. Costanzi, K. A. Jacobson, Org. Biomol. Chem., 2005, 3, 2016-2025.

- (a) K. C. Nicolaou, M. O. Frederick, R. J. Aversa, Angew. Chem. Int. Ed., 2008, 47, 7182-7225; (b) S. P. Roche, J. A. Porco Jr., Angew. Chem. Int. Ed., 2011, 50, 4068-4093.

- (a) G. Bartoli, C. Cimarelli, E. Marcantoni, G. Palmieri, M. Petrini, J. Org. Chem. 1994, 59, 5328-5335; (b) M. Liu, M. P. Sibi, Tetrahedron, 2002, 58, 7991-8035; (c) S. M. Hecht, Acc Chem Res 1986, 19, 383-391.

- (a) Y. -F. Wang, T. Izawa, S. Kobayashi, M. Ohno, J. Am. Chem. Soc., 1982, 104, 6465-6466; (b) S. Hashiguchi, A. Kawada, H. Natsugari, Perkin Trans I, 1991, J. Chem. Soc., 1991, 2435-2444; (c) G. Cardillo, C. Tomasini, Chem. Soc. Rev., 1996, 25, 117-128.

- (a) E. L. Eliel, X. -C. He, J. Org. Chem., 1990, 55, 2114-2119; (b) Y. Hayashi,; J. J. Rode, E. J. Corey, J. Am. Chem. Soc., 1996, 118, 5502-5503; (c) M. Genov, V. Dimitrov, V. Ivanova, Tetrahedron: Asymmetry, 1997, 8, 3703-3706.

- (a) E. F. Kleinmann, Comprehensive Organic Synthesis, B. M.,Trost, (Ed.), Pergamon: New York, NY, 1991;, pp 893-951; (b) I. Ojima, β-Lactam synthon method: enantiomerically pure β-lactams as synthetic intermediates. In Organic Chemistry of β-lactams; G. I., Georg, Ed.; VCH: New York, NY, 1993; pp 197-255; (c) E. J. Corey, G. A. Reichard, Tetrahedron Lett., 1989, 30, 5207-5210.

- (a) S. Ben Gharbia, R. Besbes,J. Villiéras, H. Amri, Synth. Commun., 1996, 26, 1685-1692; (b) S. Hbaïeb, Z. Latiri, H. Amri, Synth. Commun., 1999, 6, 981-988; (c) H. Kraiem, I. M. Abdullah, Tetrahedron Lett., 2003, 44, 553-555; (d) A. Arfaoui, F. Béji, T. Ben Ayed, H. Amri, Synth. Commun., 2008, 38, 3717-3725; (e) A. Fray, J. Ben Kraïem, H. Amri, Heteroatom Chem., 2013, 24, 460-465; (f) A. Arfaoui, H. Amri, Synth. Commun., 2015, 45, 2627-2635; (g) K. Jebali, A. Planchat, H. Amri, M. Mathé-Allainmat, J. Lebreton, Synthesis, 2016, 48, 1502-1517.

- M. Ameur, A.Arfaoui, H. Amri, Arkivoc, 2014, (v), 199-209.

- D. Banerjee, R. V. Jagadeesh, K. Junge, H. Junge, M. Beller, Chem. Sus. Chem., 2012, 5, 2039-2044.

- (a) K. Kobayashi, K. A. Miyazama, H. Terrahara, H. Mishime, H. Kurihare, Tetrahedron Lett., 1976, 17, 537-540; (b) R. R. Rsndo,; F. J. Bangerter, Am. Chem. Soc., 1976, 98, 6762-6764; (c) R. R. Rando, F. Bangaeter, J. Am. Chem. Soc., 1977, 99, 5141-5145; (d) R. D. Allan, G. A. R. Johnstone, B. Twitchin, Neurosci. Lett., 1977, 4, 51-54 CA 1977, 86, p 15039o.

- (a) T. Hashimoto, S. Kondo, H. Naganawa, T. Takita, K. Maede, H. Umezawa, J. Antibiot., 1974, 27, 86-87; (b) T. Hashimoto, S. Takahashi, H. Naganawa, T. Kakita, H. Umezawa, J. Antibiot., 1972, 25, 350-355; (c) C. Y. P. Teng, B. Garmen, Tetrahedron Lett., 1982, 23, 313-316.

- T. Kondo, H. Nakai, Tetrahedron, 1973, 29, 1801-1806.

- D.; E. Natalie, S. C. Donna, M. Khurana, N. S. Noha, P. S. James, J. H. Sylvia, N. Abraham, S. T. Robert, A. M. Jacqueline, Eur. J. Med. Chem., 2003, 38, 49-64.

- G. Dannhardt, A. Bauer, Nowe, U. J. Prakt. Chem., 1998, 340, 256-263.

- D. L. Boger, T. Ishizaki, J. R. Wysoki, S. A. Munk, O. Suntornwat, J. Am. Chem. Soc., 1989, 111, 6461-6463.

Downloads

Published

2016-05-20

Issue

Section

Organic Chemistry