Dimethoxyboron bromide, (MeO)2BBr, easily prepared in excellent yield from boron tribromide and trimethyl borate, is a new, efficient, regio- and chemoselective reagent useful for the halogenative cleavage of compounds containing epoxy groups into vicinal bromohydrins in the presence of ether, acetal, ketal, N-oxide, and sulfoxide groups, at low temperatures (–78°C).
(a) CoreyE.J., MarfatA., FalckJ.R., and AlbrightJ.O., J. Am. Chem. Soc., 1980, 102, 1433; (b) D. Momose and Y. Yamada, Tetrahedron, 1983, 24, 2669; (c) Y. Ueda and S.C. Maynard, Tetrahedron Lett., 1988, 29, 5197; (d) C. Venturello and R. D'Aloisio, Synthesis, 1985, 33; (e) E.J. Corey and J. Das, Tetrahedron Lett., 1982, 23, 4217; (f) J.P. Konopelski, M.A. Boehler and T.M. Tarasow, J. Org. Chem., 1989, 54, 4966; (g) J. Mann, Chem. Soc. Rev., 1987, 16, 381.
2.
BoniniC., and RighiG., Synthesis, 1994, 225, and references cited therein.
(a) JorapurV.S., and ShaligramA.M., Ind. J. Chem.1980, 19B, 906; (b) H.R. Nace and G.A. Crosby, J. Org. Chem., 1979, 44, 3105.
5.
(a) SistiA.J., and RuschG.M., J. Org. Chem., 1974, 39, 1182, and references cited therein; (b) A.J. Sisti and A.C. Vitale, J. Org. Chem., 1972, 37, 4091.
6.
(a) SharghiH., MassahA.R., EshghiH., and NiknamK., J. Org. Chem., 1998, 63, 1455; (b) H. Kotsuki, T. Shimanouchi, R. Ohshima and S. Fujiwara, Tetrahedron, 1998, 54, 2709; (c) D.R. Dalton, V.P. Dutta and D.C. Jones, J. Am. Chem. Soc., 1968, 90, 5498; (d) R.D. Rieke, W.R. Klein and T.C. Wu, J. Org. Chem., 1993, 58, 2492; (e) D.R. Dalton, R.K. Rodebaugh and C.W. Jefford, J. Org. Chem., 1972, 37, 362; (f) D.R. Dalton and V.P. Dutta, J. Chem. Soc. B, 1971, 85; (g) N. Iranpoor, F. Kazemi and P. Salehi, Synth. Commun., 1997, 27, 1247 and references cited therein.
7.
(a) SabithaG., BabuR.S., RajkumarM., ReddyC.S., and YadavJ.S., Tetrahedron Lett., 2001, 42, 3955; (b) M.A. Reddy, K. Surendra, N. Bhanumathi and K.R. Rao, Tetrahedron, 2002, 58, 6003; (c) J.M.B. Yacoubou, N. Maduike, S. Kyere, L. Doan and D.L. Whalen, Tetrahedron Lett., 2002, 43, 3781; (d) K. Niknam and T. Nasehi, Tetrahedron, 2002, 58, 10259; (e) Y. Tomata, M. Sasaki, K. Tanino and M. Miyashita, Tetrahedron Lett., 2003, 44, 8975; (f) H. Sharghi, M.M. Eskandari and R. Ghavami, J. Mol. Catal. A, 2004, 215, 55; (g) M. Soroka and W. Goldeman, Tetrahedron, 2005, 61, 4233.
8.
BhattM.V., and KulkarniS.U., Synthesis, 1983, 249.
9.
(a) MandalA.K., SoniN.R., and RatnamK.R., Synthesis, 1985, 275; (b) T.W. Bell and J.A. Ciaccio, Tetrahedron Lett., 1986, 27, 827; (c) Y. Guindon, M. Therien, Y. Girard and C. Yoakim, J. Org. Chem., 1987, 52, 1680; (d) N.N. Joshi, M. Srebnik and H.C. Brown, J. Am. Chem. Soc., 1988, 110, 6246; (e) M. Srebnik, N.N. Joshi and H.C. Brown, Israel J. Chem., 1989, 29, 229; (f) P. Bovicelli, E. Mincione and G. Ortaggi, Tetrahedron Lett., 1991, 32, 3719.
10.
BrownH.C., and RoyC.D., Molecules Online, 1998, 2, 114, and references cited therein.