| T1593 | 4-Trifluoromethylbenzoic Anhydride (1) |
10g |
| M1439 | 2-Methyl-6-nitrobenzoic Anhydride (2) |
5g 1g |
Recently, Shiina et al. have been reported a new condensation method using dehydrating condensing agents 1 and 2. In the presence of 1 or 2, carboxylic acids react with nearly equimolar amounts of alcohols or amines to obtain corresponding carboxylic esters or amides in high yields.
1 and 2 perform effectively under Lewis acidic conditions and basic conditions, respectively. Therefore, a wide variety of substrates can be used by choosing 1 and 2.


This method also applies to intramolecular reactions. For example, 1 and 2 have been used the synthesis of the lactone moieties of cephalosporolide D and octalactin B, respectively.
1 and 2 are easy to handle, and condensation reactions using these reagents in this simple procedure have obtained desired products in high yields. 1 and 2 are quite effective as dehydrating condensing agents in the synthesis of carboxylic esters and amides, especially, when synthesizing lactones and lactams.
References
anhydride
a)I. Shiina, S. Miyoshi, M. Miyashita, T. Mukaiyama, Chem. Lett., 1994, 515.
b)I. Shiina, M. Miyashita, M. Nagai, T. Mukaiyama, Heterocycles, 40, 141
(1995).
c)I. Shiina, H. Fujisawa, T. Ishii, Y. Fukuda, Heterocycles, 52, 1105 (2000).
d)I. Shiina, Tetrahedron, 60, 1587 (2004).
2) Condensation reaction by using 2-methyl-6-nitrobenzoic
anhydride
a)I. Shiina, R. Ibuka, M. Kubota, Chem. Lett., 2002, 286.
b) J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Org. Lett., 5, 3021
(2003).
c)I. Shiina, H. Oshiumi, M. Hashizume, Y. Yamai, R. Ibuka, Tetrahedron Lett.,
45, 543 (2004).
d)I. Shiina, Tetrahedron, 60, 4729 (2004).
e)I. Shiina, M. Kubota, H. Oshiumi, M. Hashizume, J. Org. Chem., 69, 1822
(2004).
f) I. Shiina, M. Hashizume, Y. Yamai, H. Oshiumi, T. Shimazaki, Y. Takasuna, R. Ibuka, Chem. Eur. J., 11, 6601 (2005).
g) Tokyo Kasei Kogyo Co., Ltd, JP Patent 2003-335731.
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