Bifunctionalized Allenes. Part XXIII. An Efficient Method for Regioselective Synthesis of 5-Phosphorylated Allenecarboxylates

[1] (a) Patai, S., Ed. The Chemistry of Ketenes, Allenes and Related Compounds; John Wiley & Sons: New York, 1980; (b) Landor, S. R. Ed. The Chemistry of the Allenes; Academic Press: London, 1982, Vol. 1-3; (c) Pasto, D. J. Tetrahedron1984, 40, 2805-2827; (d) Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley & Sons: New York, 1988; (e) Zimmer, R. Synthesis1993, 165-178; (f) Elsevier, C. J. Methods of Organic Chemistry (Houben-Weyl); Vol. E21a, Helmchen, R.W.; Mulzer, J.; Schaumann, E., Eds., Thieme: Stuttgart, 1995, 537-566; (g) Krause, N.; Hashmi, A. S. K., Eds. Modern Allene Chemistry; Wiley-VCH: Weinheim, 2004, Vol. 1 & 2; (h) Brummond, K. M.; DeForrest, J. E. Synthesis2007, 795-818.Search in Google Scholar

[2] (a) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev.2002, 31, 12-21; (b) Petrov, P. Y.; Angelov, C. M.; Petrov, G.; Alexiev, A.; Cavell, R. G. Heteroatom Chem.2004, 15, 413-417; (c) Ma, S. Aldrichimica Acta2007, 40, 91-102; (d) Hassan, H. H. A. M. Curr. Org. Synth.2007, 4, 413-439; (e) Petrov, P. Y.; Angelov, C. M.; McDonald, R.; Alexiev, A.; Cavell, R. G. Heteroatom Chem.2010, 21, 196-202; (f) Back, T. G.; Clary, K. N.; Gao, D. Chem. Rev.2010, 110, 4498-4553;Search in Google Scholar

[3] (a) Bestmann, H. J.; Hartung, H. Angew. Chem. Int Ed.1963, 2, 214-215; (b) Aksnes, G.; Froeyen, P. Acta Chim. Scand.1968, 22, 2347-2347; (c) Lang, R. W.; Hansen, H. -J. Helv. Chim. Acta1980, 63, 438-455.Search in Google Scholar

[4] Fillion, H.; Hseine, A.; Pera, M. -H.; Dufaud, V.; Refouvelet, B. Synthesis1987, 708-709.10.1055/s-1987-28052Search in Google Scholar

[5] Tanaka, K.; Otsubo, K.; Fuji, K. Synlett1995, 933.10.1055/s-1995-5140Search in Google Scholar

[6] Li, C. -Y.; Wang, X. -B.; Sun, X. -L.; Tang, Y.; Zheng, J. -C.; Xu, Z. -H.; Zhou, Y. -G.; Dai, L. -X. J. Am. Chem. Soc.2007, 129, 1494-1495.10.1021/ja068642v17283983Search in Google Scholar

[7] Miesch M. Synthesis2003, 746-752 and references cited therein.10.1055/s-2004-815983Search in Google Scholar

[8] (a) Mark, V. The Uncatalyzed Rearrangements of Tervalent Phosphorus Esters in Selective Organic Transformations; Thyagarajan, B. S., Ed., John Wiley & Sons: New York, 1970, pp. 319-437; (b) Landor, P. D. in The Chemistry of the Allenes, Vol. 1, Landor, S. R., Ed., Academic Press: New York, 1982, pp. 174-178; (d) Saalfrank, R. W.; Lurz, C. -J. in Methoden der Organischen Chemie (Houben Weyl), Kropf, H.; Scheumann, E., Eds., Thieme: Stuttgart, 1993, pp. 2959-3102; (e) Hashmi, A. S. K. Synthesis of Allenes in Modern Allene Chemistry, Vol. 1, Krause, N.; Hashmi, A. S. K., Eds., Wiley-VCH: Weinheim, 2004, pp. 3-50.Search in Google Scholar

[9] (a) Pudovik, A. N.; Aladjeva, I. M. J. Gen. Chem.1963, 33, 700-706; (b) Macomber, R. S. J. Am. Chem. Soc. 1977, 99, 3072-3075; (c) Denmark, S. E.; Marlin, J. E. J. Org. Chem. 1991, 56, 1003-1013; (d) Cai, B.; Blackburn, G. M. Synth. Commun.1997, 27, 3943-3949; (e) Saalfrank, R. W. Haubner, M. Deutscher, C. Bauer, U. Eur. J. Org. Chem.1999, 2367-2372.Search in Google Scholar

[10] (a) Boiselle, A. P.; Meinhardt, N. A. J. Org. Chem.1962, 27, 1828-1833; (b) Mark, V. Tetrahedron Lett.1962, 281-284; (c) Sevin, A.; Chodkiewicz, W. Bull. Soc. Chim. Fr.1969, 4016-4021; (d) Ignatev, V. M.; Timofeeva, T. N.; Ionin, B. I.; Petrov, A. A. J. Gen. Chem.1969, 39, 1567-1572.Search in Google Scholar

[11] (a) Nicolaou, K. C.; Maligres, P.; Shin, J; de Leon, E.; Rideout, D. J. Am. Chem. Soc.1990, 112, 7825-7826; (b) Curfin, M. L.; Okamura, W. H. J. Org. Chem.1990, 55, 5278-5287; (c) Grissom, J. W.; Huang, D. Angew. Chem. Int. Ed.1995, 34, 2037-2039; (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synthesis1996, 711-714; (e) de Frutos, O.; Echavarren, A. M. Tetrahedron Lett.1997, 38, 7941-7943; (f) Schmittel, M.; Steffen, J.-P.; Maywald, M.; Engels, B.; Helten, H.; Musch, P. J. Chem. Soc. Perkin Trans. 22001, 1331-1342.Search in Google Scholar

[12] Ismailov, I. E.; Ivanov, I. K.; Christov, V. Ch. Bulg. Chem. Commun.2014,46, Special Issue A, 39-46.Search in Google Scholar

[13] Hasanov, H. H.; Ivanov, I. K.; Christov, V. Ch. Bulg. Chem. Commun.2017,49, Special Issue B, 25-32.Search in Google Scholar

[14] Hasanov, H. H.; Ivanov, I. K.; Christov, V. Ch. Bulg. Chem. Commun.2019,51(4), in press.Search in Google Scholar

[15] Ismailov, I. E.; Ivanov, I. K.; Christov, V. Ch. Bulg. Chem. Commun.2017,49, Special Issue B, 33-41.Search in Google Scholar

[16] Previous our reports on the chemistry of bifunctionalized allenes, see: (a) Christov, V. Ch.; Prodanov, B. Phosphorus, Sulfur, Silicon2000, 166, 265-273; (b) Christov, V. Ch.; Prodanov, B.; Nikolova, R. Phosphorus, Sulfur, Silicon2000, 166, 275-281; (c) Christov, V. Ch.; Prodanov, B. Phosphorus, Sulfur, Silicon2000, 166, 243-249; (d) Christov, V. Ch.; Prodanov, B. Heterocyclic Commun.2002, 8, 349-354; (e) Christov, V. Ch.; Prodanov, B. Heterocycles2002, 57, 1777-1780; (f) Christov, V. Ch.; Prodanov, B. Synth. Commun.2004, 34, 1577-1588; (g) Christov, V. Ch.; Ivanova, J. G. Synth. Commun.2006, 36, 2231-2244; (h) Ivanov, I. K.; Christov, V. Ch. Phosphorus, Sulfur, Silicon2013, 188, 913-919; (i) Hasanov, H. H; Ivanov, I. K.; Christov, V. Ch. Heteroatom Chem.2017, 28, e21357, 1-10; (j) Hasanov, H. H.; I. E.; Ivanov, I. K.; Christov, V. Ch. Phosphorus, Sulfur, Silicon2019, 193, 611-619; (k) Hasanov, H. H.; I. E.; Ivanov, I. K.; Christov, V. Ch. Phosphorus, Sulfur, Silicon2019, 193, 797-805.Search in Google Scholar

[17] (a) Metcalf, B. W.; Wright, C. L.; Burkhart, J. P.; Johnston, J. O. J. Am. Chem. Soc.1981, 103, 3221-3222; (b) Muller, M.; Mann, A.; Taddei, M. Tetrahedron Lett.1993, 34, 3289-3290; (c) Brel, V. K.; Stang, P. J. Eur. J. Org. Chem.2003, 224-229; (d) Brel, V. K. Synthesis2001, 1539-1545; (e) Brel, V. K.; Belsky, V. K.; Stash, A. I.; Zvodnik, V. E.; Stang, P. J. Org. Biomol. Chem.2003, 1, 4220-4226; (f) Brel, V. K.; Belsky, V. K.; Stash, A. I.; Zvodnik, V. E.; Stang, P. J. Eur. J. Org. Chem.2005, 512-521.Search in Google Scholar

[18] (a) Christov, V. Ch.; Ivanov, I. K. Phosphorus, Sulfur, Silicon2002, 177, 2445-2454; (b) Christov, V. Ch.; Ivanov, I. K. Sulfur Lett.2002, 25, 191-198; (c) Christov, V. Ch.; Ivanov, I. K. Heterocyclic Commun.2003, 9, 629-634; (d) Christov, V. Ch.; Ivanov, I. K. Phosphorus, Sulfur, Silicon2004, 179, 1681-1690; (e) Ivanov, I. K.; Christov, V. Ch. Heteroatom Chem.2012, 23, 345-351; (f) Ivanov, I. K.; Christov, V. Ch. Synth. Commun.2013, 43, 800-809.Search in Google Scholar