A microwave-promoted Reformatsky reaction of aldehydes and ketones with ethyl bromoacetate, in the absence of solvent, using activated zinc metal and solid NH4Cl afforded the corresponding β-hydroxyesters in good to excellent yields.
(a) ShrinerR.L., Org. React., 1942, 1, 1; (b) W. J. Gensler, Chem. Rev., 1957, 57, 265; (c) M. W. Rathke, Org. React., 1975, 22, 423; (d) D. G. M. Diaper and A. Kuksis, Chem. Rev., 1959, 59, 89.
2.
(a) BeckerD., BrodskyN., and KaloI., J. Org. Chem., 1978, 43, 2557; (b) A. Barco, S. Bennet and G. P. Pollini, J. Org. Chem., 1980, 45, 4776; (c) D. K. Klipa and H. J. Hart, J. Org. Chem., 1981, 46, 2815; (d) J. S. Witzemann and W. D. Nottingham, J. Org. Chem., 1989, 54, 3258 and references cited therein; (e) F. G. West and G. V. Gunawardena, J. Org. Chem., 1993, 58, 5043.
3.
(a) AdamaF., and AlbertoB., Pure Appl. Chem., 1999, 71, 573; (b) S. L Cresswell and S. J. Haswell, Chem. Ind. (London), 1999, 16, 621; (c) R. S. Varma, Green Chem., 1999, 7, 43; (d) C. R. Strauss, Aust. J. Chem., 1999, 52, 83.
4.
(a) GiguereR.J., BrayT. L., DuncanS. M., and MajetichG., Tetrahedron Lett., 1986, 27, 4945; (b) R. J. Giguere, A. M. Namen, B. O. Lopez, A. Arepally, D. E. Ramos, G. Majetich and J. Defauw, Tetrahedron Lett., 1987, 28, 6553; (c) R. J. Giguere, Organic Synthesis: Theory and Applications, HudlickyT., (Ed.), JAI Press Inc.: Greenwich, CT, 1989, 1, 103; (d) R. N. Gedye, F. E. Smith and K. C. Westaway, Can. J. Chem., 1988, 66, 17; (e) R. N. Gedye, F. E. Smith, K. C. Westaway, H. Ali, L. Baldisera, L. Laberge and J. Rousell, Tetrahedron Lett., 1986, 27, 279; (f) R. N. Gedye, W. Rank and K. C. Westaway, Can. J. Chem., 1991, 69, 706; (g) A. B. Alloum, B. Labiad and D. J. Villemin, J. Chem. Soc. Chem. Commun., 1989, 386; (h) J. Berlan, P. Giboreau, S. Lefervre and C. Marchand, Tetrahedron Lett., 1991, 32, 2363; (i) S. T. Chen, H. H. Chiou and K. T. Wang, J. Chem. Soc. Chem. Commun., 1990, 807; (j) E. Gutierrez, A. Loupy, G. Bram and E. Ruiz-Hitzky, Tetrahedron Lett., 1989, 30, 945; (k) G. Bram, A. Loupy, M. Majdoub, E. Gutierrez and E. Ruiz-Hitzky, Tetrahedron Lett., 1990, 46, 5167; (l) K. Tanaka and F. Toda, Chem. Rev., 2000, 100, 1025; (m) M. M. Heravi, D. Ajami, B. Mohajerani, K. Tabar-Hydar and M. Ghassemzadeh, Synth. Commun., 2002, 32, 3325; (n) J. F. Zhou, Z. C. Zou and J. C. Feng, Synth. Commun., 2002, 32, 3389.
5.
(a) HaradaT., and MukaiyamaT., Chem. Lett., 1982, 161; (b) Z. Shen, J. Zhang, H. Zou and M. Yang, Tetrahedron Lett., 1997, 38, 2733; (c) S. Araki, H. Ito and Y. Butsugan, Synth. Commun., 1988, 18, 453; (d) H. Schick, R. Ludwig, K.-H. Schwarz, K. Kleiner and A. Kunath, Angew. Chem. Int. Ed. Engl., 1993, 32, 1191; (e) T. Tabuchi, K. Kawamura, J. Inanaga and M. Yamaguchi, Tetrahedron Lett., 1986, 27, 3889; (f) X. Huang, L. Xie and H. Wu, Tetrahedron Lett., 1987, 28, 801; (g) K. Marioka, S. Hashimoto, Y. Kitagawa, H. Yamamoto and H. Nozaki, J. Am. Chem. Soc., 1977, 99, 7705; (h) T. Gabriel and L. Wessjohann, Tetrahedron Lett., 1997, 38, 1363; (i) T. Gabriel and L. Wessjohann, Tetrahedron Lett., 1997, 38, 4387; (j) S. Araki, N. Katsumura, K. Kawasaki and Y. Butsugan, J. Chem. Soc. Perkin Trans. 1, 1991, 499; (k) S. Araki, H. Ito, N. Katsumura and Y. Butsugan, J. Organomet. Chem., 1989, 369, 291; (l) H. B. Kagan, J.-L. Namy and P. Girard, Tetrahedron, 1981, 37, 175; (m) T. Imamoto, T. Kusumoto, T. Tawarayama, Y. Sugiura and M. Yokoyama, J. Org. Chem., 1984, 49, 3904; (n) P. S. Johar, S. Araki and Y. Butsugan, J. Chem. Soc. Perkin Trans. 1, 1992, 711; (o) G. Cahiez and P.-Y. Chavant, Tetrahedron Lett., 1989, 30, 7373; (p) G. A. Molander and J. B. Etter, J. Am. Chem. Soc., 1987, 109, 6556; (q) J. Nokami, T. Tamaoka, H. Ogawa and S. Wakabayashi, Chem. Lett., 1986, 541; (r) L.-C. Chao and R. D. Rieke, J. Org. Chem., 1975, 40, 2253; (s) P. H. Lee, K. Bang, K. Lee, S. Sung and S. Chang, Synth. Commun., 2001, 31, 3781; (t) R. D. Rieke and S. J. Uhm, Synthesis, 1975, 452; (u) A. Fustner, Synthesis, 1989, 571; (v) A. Fustner, Angew. Chem. Int. Ed. Engl., 1993, 32, 164.
6.
(a) NishiyamaT., WoodhallJ. F., LawsonE. N., and KitchingW., J. Org. Chem., 1989, 54, 2184; (b) B. H. Han and P. Boudjouk, J. Org. Chem., 1982, 47, 5030.
7.
BoseA.K., GuptaK., and ManhasM. S., J. Chem. Soc. Chem. Commun., 1984, 86.
8.
KitazumeT., Synthesis, 1986, 855.
9.
HuangY-Z., and LiaoY., J. Org. Chem., 1991, 56, 1381 and references cited therein.
10.
WatanabeS., SugaK., FujitaT., and FujiyoshiK., Israel Journal of Chemistry, 1970, 8(4), 731 and references cited therein.
11.
FukuzawaS., and HiraiK., J. Chem. Soc., Perkin Trans. 1, 1993, 17, 1963.
12.
RiekeR.D., and UhmS. J., Synthesis, 1975, 7, 452 and references cited therein.
13.
CarrG., and WhittakerD., J. Chem. Soc., Perkin Trans. 2, 1989, 4, 359.
14.
MiyashiT., NishizawaY., FujiiY., YamakawaK., KamataM., AkaoS., and MukaiT., J. Am. Chem. Soc., 1986, 108, 1617.