A new solid-phase synthetic method using Mukaiyama's reagent under mild conditions is reported to prepare amides in high purity without purification after cleavage from the resins.
For reviews, see (a) MerrifieldR.B., Angew. Chem., Int. Ed. Engl., 1985, 24, 799; (b) G. B Fields and R. L. Noble, Int. J. Pept. Protein Res., 1990, 35, 161; (c) G. Jung and A. Becksickinger, Angew. Chem., Int. Ed. Engl., 1992, 31, 367.
2.
For reviews, see (a) FruchtelJ.S., and JungG., Angew. Chem., Int. Ed. Engl., 1996, 35, 17; (b) L. A. Thompson and J. A. Ellman, Chem. Rev., 1996, 96, 555; (c) P. H. H. Hermkens, H. C. J. Ottenheijm, and D. C. Rees, Tetrahedron, 1996, 52, 4527; (d) P. H. H. Hermkens, H. C. J. Ottenheijm, and D. C. Rees, Tetrahedron, 1997, 53, 5643; (e) S. Booth, P. H. H. Hermkens, H. C. J. Ottenheijm, and D. C. Rees, Tetrahedron, 1998, 54, 15385; (f) B. A. Lorsbach and M. J. Kurth, Chem. Rev., 1999, 99, 1549; (g) F. Guillier, D. Orian, and M. Bradley, Chem. Rev., 2000, 100, 2091. (h) R. E. Sammelson and M. J. Kurth, Chem. Rev., 2001, 101, 137; for books, see (i) D. Obrecht and J. M. Villalgordo, Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecule-Weight Compound Libraries; Elsevier Science Ltd.: Oxford, 1998; (j) K. Burgess, Solid-Phase Organic Synthesis; Wiley, New York, 2000.
3.
VlattasI., DellureficioJ., DunnR., SytwuI. I., and StantonJ., Tetrahedron Lett., 1997, 38, 7321.
4.
HudsonD., J. Org. Chem., 1988, 53, 617.
5.
(a) CastroB., DormoyJ. R., and SelveG. E. C., Tetrahedron Lett., 1975, 1219. (b) P. Rivaille, J. P. Gautron, B. Castro, and G. Milhand, Tetrahedron, 1980, 36, 3413.
6.
(a) CosteJ., Le-NguyenD., CastroB., Tetrahedron Lett., 1990, 31, 205; (b) B. O. Scott, A. C. Siegmund, C. K. Marlowe, Y. Pei, and K. L. Spear, Mol. Diversity, 1995, 1, 125.
7.
KnorrR., TrzeclakA., BannwarthW., and GillessenD., Tetrahedron Lett., 1989, 30, 1927.
8.
(a) CarpinoL.A., El-FahamA., MinorC. A., and AlbericioF., J. Chem. Soc., Chem. Commun., 1994, 201; (b) L. A. Carpino, J. Am. Chem. Soc., 1993, 115, 4397.
9.
For review, see (a) MukaiyumaT., Angew. Chem., Int. Ed. Engl., 1979, 18, 707. For the application for formation of amides, see (b) E. Bald, K. Saigo, and T. Mukaiyama, Chem Lett., 1975, 1163.
10.
The original procedure without using TMOF: (a) CheneraB., FinkelsteinJ. A., and VeberD. F., J. Am. Chem. Soc., 1995, 117, 11999; (b) A. M. Fivush and T. M. Wilson, Tetrahedron Lett., 1997, 38, 7151.
11.
LiP., and XuJ.-C., Tetrahedron, 2000, 56, 8119.
12.
BartonD.H. R., JaszberenyiJ. C., TheodorakisE. A., and ReibenspiesJ. H., J. Am. Chem. Soc., 1993, 115, 8050.
13.
NarasakaK., HiroseT., UchimuruT., and MukaiyamaT., Chem. Lett., 1982, 991.
14.
McCoubreyA., and MathiesonD. W., J. Chem. Soc., 1949, 696.
15.
WakayamaM., MasakazuH., SuzukiI., and ShibuyaM., Heterocycles, 1999, 51, 325.
16.
GayR.L., and HauserC. R., J. Am. Chem. Soc., 1967, 89, 1647.
