Highly diastereoselective synthesis of N-substituted 4-(diethoxyphosphoryl)-pyrrolidines-3-carboxylate starting from tetraethyl methylenediphosphonate
DOI:
https://doi.org/10.13171/mjc.2.1.2012.29.07.16Abstract
 This paper describes a convenient synthesis of novel series of 3,4-disubstituted pyrrolidines based on the aza-Michael addition of primary amines to 3,4-difunctionalized-1,3-diene followed by an intramolecular cyclization.References
Z. Wang, A. Lucassen, L. Zhang, J. Yang, K. kohse-Höinghaus, f. Qi Proceedings of the Combustion Institute 2011, 33, 415-423.
(a) J. R. Lewis Nat. Prod. Rep. 2001, 18, 95, (b) D. O’Hagan Nat. Prod. Rep 2000, 17, 435-446.
(a) A. K. Podichetty, S. Wagner, S. Schröer, A. Faust, M. Schäfers, O. Schober, K. Kopka, G. Haufe, J. Med. Chem. 2009, 52, 3484-3495, (b) J. I. Venäläinen, E. A.
Wallén, A. A. Poso, J. A. GarcÃa-Horsman, P. T. Männistö, T. J. Med. Chem. 2005, 48, 7093-7095.
J. Obniska, K. Kaminski, D. Skrzynska, J. Pichor Eur. J. Med. Chem. 2009, 44, 2224-2233, (b) K. Kaminski, J. Obniska Bioorg. Med. Chem. 2008, 16, 4921-4931.
F. Z. Liu, H. Fang, H. W. Zhu, Q. Wang, Y. Yang, W. F. Xu Bioorg. Med. Chem. 2008, 16, 578-585.
G. T. Warner, C. M. Perry Drugs 2002, 62, 1381-1405.
(a) G. Pandey, P. Banerjee, S. R. Gadre Chem. Rev. 2006, 106, 4484-4517, (b) F. Bellina, R. Rossi Tetrahedron 2006, 62, 7213-7256, (c) S. Husinec, V. Savic Tetrahedron: Asymmetry 2005, 16, 2047-2061, (d) F. -X. Felpin, J. Lebreton J. Eur. J. Org. Chem. 2003, 3693-3712.
(a) M. Takimoto, Y. Nakamura, K. Kimura, M. Mori J. Am. Chem. Soc. 2004, 126, 5956-5957, (b) R. Pedrosa, C. Andres, L. Martin, J. Nieto, C. Roson J. Org. Chem. 2005, 70, 4332-4337, (c) J. Montgomery, M. Song Org. Lett. 2002, 4, 4009-4011.
(a) G. Zhu, Z. Zhang Org. Lett. 2004, 6, 4041-4044, (b) Q. Yang, H. Alper, W. -J Xiao Org. Lett. 2007, 9, 769-771.
R. Pedrosa, C. Andre´s, J. P. Duque-Soladana, P. Mendiguchia Eur. J. Org. Chem. 2000, 3727-3730.
(a) S. E. Denmark, L. E. Marcin J. Org. Chem. 1995, 60, 3221-3235. (b) J. Gebauer, P. Dewi, S. Blechert Tetrahedron Lett. 2005, 46, 43-46.
F. A. Davies, Y. Wu, H. Xu, J. Zhang Org. Lett. 2004, 6, 4523-4525.
(a) J. H. Kim, M. J. C. Long, J. Y. Kim, K. H. Park Org. Lett. 2004, 6, 2273-2276. (b) B. Schlummer, J. F. Hartwig Org. Lett. 2002, 4, 1471-1474.
(a) G. B. Bajracharya, Z. Huo, Y. Yamamoto J. Org. Chem. 2005, 70, 4883-4886. (b) J. A. Bexrud, J. D. Beard, D. C. Leitch, L. L. Schafern Org. Lett. 2005, 7, 1959-1962. (c)J. Y. Kim, T. Livinghouse Org. Lett. 2005, 1737-1739.
B. Tarnchompoo, C. Thebtaranonth, Y. Thebtaranonth Tetrahedron Lett. 1987, 28, 6675-6678.
B. Tarnchompoo, C. Thebtaranonth, Y. Thebtaranonth Tetrahedron Lett. 1987, 28, 6671-6679.
M. Kotera, J. M. Lehn, J. P. Vigneron Tetrahedron 1995, 51, 1953-1972.
W. J. Bailey, R. L. Hudson, E. T. Yates J. Org. Chem. 1963, 28, 828-831.
X. Zhang, R. C. Larock Org Lett. 2003, 5, 921-923.
C. Yu, D. K. P. Ng, B-L Chen, T-Y. Luh Organometallics 1994, 13, 1487-1497.
B. E. Sime, B. Rickborn, J. M. Flournoy, I. B. Berlman J. Org. Chem. 1988, 53, 4613-4616.
Z. Rappoport The chemistry of dienes and polyenes,. Chichester: John Wiley & Sons, 1997, 1, 1-1058.
Z. Rappoport The chemistry of dienes and polyenes, vol. 2. Chichester: John Wiley & Sons, 2001.
F. Beji, J. Lebreton, J. Villièras, H. Amri Tetrahedron 2001, 57, 9959-9962.
U. UrÅ¡iÄ, U. GroÅ¡elji, A. Meden, J. Svete, B. Stanovnik Tetrahedron Lett. 2008, 49, 3775-3778.
D. P. J. Hamon, P. R. Spurr Synthesis 1981, 873-879.
R. M. Davidson, G. L. Kenyon J. Org. Chem. 1977, 42, 1030-1035.
M. F. Semmelhack, P. Helquist, L. D. Jones, L. Keller, L. Mendelson, L. S. Ryono, J. G. Smith, R. D. Stauffer J. Am. Chem. Soc. 1981, 103, 6460-6471.
R. L. Cobb, J. E. Mahan J. Org. Chem. 1977, 42, 2829-2832.
D. Bellus, C. D. Weis Tetrahedron Lett. 1973, 14, 999-1000.
D. Bellus, K. Von Bredow, H. Sauter, C. D. Weis Helv. Chim. Acta 1973, 56, 3004-3038.
M. G. Pettett, A. B. Holmes J. Chem. Soc., Perkin Trans. 1, 1985, 1161-1165.
H. Kiji, T. Okano, E. Fujii, J. Tsuji Synthesis 1997, 869-870.
U. UrÅ¡iÄ, J. Svete, B. Stanovnik Tetrahedron 2008, 64, 9937-9946.
G. Sturtz J. Gurevenou., Synthesis 1991, 661-662.
M. R. Leadbetter, W. Brown, W. Richard, R. McKenna, M; Maureen US. Patent 5 688, 983, (1997).
A. Samarat, J. Ben Kraiem, T. Ben Ayed, H. Amri Tetrahedron 2008, 64, 9540-9543.
I. Beltaïef, R. Besbes, F. Ben Amor, H. Amri, H. Tetrahedron 1999, 55, 3949-3958.
A. Arfaoui, F. Béji, H. Amri Synth. Commun. 2010, 40, 766-771.
T. Ben Ayed, H. Amri, M. M. El Gaïed, J. Villiéras Tetrahedron 1995, 51, 9633-9642.
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