Free to Read
A novel one-pot synthetic method for α-methylenation of lactones and cycloalkanones based on thiophosphates
Ewa Krawczyk,
Aleksandra Skowrońska,
Ewa Krawczyk
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363łódź, Poland
Search for more papers by this authorCorresponding Author
Aleksandra Skowrońska
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363łódź, Poland
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363łódź, Poland; Fax: 48(42) 6847126Search for more papers by this authorEwa Krawczyk,
Aleksandra Skowrońska,
Ewa Krawczyk
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363łódź, Poland
Search for more papers by this authorCorresponding Author
Aleksandra Skowrońska
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363łódź, Poland
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363łódź, Poland; Fax: 48(42) 6847126Search for more papers by this authorFirst published: 14 November 2000
Citations: 20
Abstract
A variety of lactones and cycloalkanones have been converted into their α-methylene derivatives using a one-pot procedure. In our approach, the key steps involve the formation of readily available thiophosphates and their reactions with sodium borohydride under very mild conditions. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:353–361, 2000
REFERENCES
- 1 (a) Grieco, P. A. Synthesis 1975, 67;
- 2(b) Hoffmann, H. M. R.; Rabe, J. Angew Chem Int Ed Engl 1985, 24, 94;
- 3(c) Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157.
- 2 Tomioka, K.; Masumi, F.; Yamashita, T.; Koga, K. Tetrahedron Lett 1984, 25, 333.
- 3 Righby, J. H.; Wilson, J. Z. J Am Chem Soc 1984, 106, 8217.
- 4 Parker, V. L.; Johnson, F. J. J Org Chem 1973, 38, 2489.
- 5 Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. Synthetic Commun 1993, 23, 495.
- 6(a) Paterson, I.; Fleming, I. Tetrahedron Lett 1979, 993;
- 9(b) Paterson, I. Tetrahedron 1988, 44, 4207.
- 7(a) Edgar, M. T.; Greene, A. E.; Crabbe, P. J Org Chem 1979, 44, 159;
- 11(b) Arido, M.; Akahane, A.; Yamaoka, H.; Takase, K. J Org Chem 1982, 47, 3909.
- 8 Tsuji, J.; Nisar, M.; Minami, I. Tetrahedron Lett 1986, 27, 2483.
- 9 Dybowski, P.; Skowrońska, A. Tetrahedron Lett 1991, 32, 4385.
- 10(a) Maciagiewicz, I.; Dybowski, P.; Skowrońska, A. Tetrahedron Lett 1999, 40, 3791, and references cited therein;
- 15(b) Dybowski, P.; Skowrońska, A. Synthesis 1997, 284;
- 16(c) Dybowski, P.; Skowrońska, A. Synthesis 1997, 1134.
- 11 In Part presented at XIII ICPC, Jerusalem, Israel: Skowrońska, A.; Krawczyk, E.; Koprowski, M.; Dybowski, P. Phosphorus Sulfur Silicon 1996, 109, 409.
- 12 Hutchinson, Ch. R. J Org Chem 1974, 39, 1854.
- 13 Chan, T. H.; Brownbridge, P. J Am Chem Soc 1980, 102, 3534.
- 14(a) Skowrońska, A.; Dembiński, R.; Gwara, J.; Michalski, J. Phosphorus Sulfur 1988, 39, 119, and references cited therein;
- 21(b) Michalski, J.; Skowrońska, A.; Łopusiński, A. Phosphorus Sulfur Silicon 1991, 58, 61, and references cited therein.
- 15(a) Knocke, H.; Ourisson, G.; Perold, G. W.; Foussereau, J.; Maleville, J. Sciences 1969, 166, 239;
- 23(b) Perold, G. W.; Muller, J. C.; Ourisson, G. Tetrahedron 1972, 28, 5797.
- 16 Kido, F.; Tsutsumi, K.; Maruta, R.; Yoshikoshi, A. J Am Chem Soc 1979, 101, 6420.
- 17 Grieco, P. A.; Hiroi, K. J. J Chem Soc Chem Commun 1972, 1317.
- 18(a) Regitz, M.; Ruter, J. Chem Ber 1968, 101, 1263.
- 27(b) Ainsworth, C. Org Synth Coll Vol 1963, 4, 536;
- 28(c) Boatman, S.; Harris, T. M.; Hauser, C. R. Org Synth Coll Vol 1973, 5, 187.
- 19 Ward, D. E.; Rhee, Ch. K. Synthetic Commun 1988, 1927.
- 20 Murray, A. W.; Reid, R. G. Synthesis 1985, 35.
- 21(a) Crisp, G. T.; Meyer, A. G. Tetrahedron 1995, 51, 5831;
- 32(b) Yu, L.-Ch.; Helquist, P. J Org Chem 1981, 46, 4536.
- 22 Csuk, R.; Schröder, Ch.; Hutter, S.; Mohr, K. Tetrahedron Asymm 1997, 8, 1411.
- 23(a) Adlington, R. M.; Baldwin, J. E.; Gansäuer, A.; McCoull, W.; Russell, A. T. J. Chem Soc Perkin Trans I 1994, 1697;
- 35(b) Tanaka, K.; Yoda, H.; Isobe, Y.; Kaji, A. J Org Chem 1986, 51, 1856.
- 24 Nakahira, H.; Ryu, J.; Ikebe, M.; Oku, Y.; Ogawa, A.; Kambe, N.; Sonoda, N.; Murai, S. J Org Chem 1992, 57, 17.
- 25 Shono, T.; Nishiguchi, I.; Komamura, T.; Sasaki, M. J Am Chem Soc 1979, 101, 984.
- 26 Pellet, M. J Chem Res 1982, 2552.
- 27 Clive, D. L. J.; Joussef, A. C. J Org Chem 1990, 55, 1096.
- 28 Stang, P. J.; Treptow, W. L. J Med Chem 1981, 468.
- 29 Tius, M. A. J Chem Soc Chem Commun 1989, 867.
