(2R,2R')-2,2'-(2-Iodo-1,3-phenylene) bis (oxy) bis (N-mesitylpropanamide)
Spirolactone can be synthesized from a hydroxynaphthyl carboxylic acid
at a high optical purity!
Asymmetric metal catalysts are used for synthesizing chiral compounds.
Rare metals such as palladium and ruthenium and detrimental elements such
as chromium, manganese and osmium have been used as metal ions. In recent
years, development of environment-conscious catalysts is explored from
the viewpoint of green chemistry.
This product is a chiral hypervalent iodine catalyst1) 2) developed by Professor
Kazuaki Ishihara, Nagoya University. When used in the enantioselective
oxidative coupling reaction (Kita spirolactonization3)) of hydroxynaphthyl
carboxylic acids developed by Professor Yasuyuki Kita, Ritsumeikan University,
asymmetry yield of 89 to 94% is achieved. This reaction gives spirolactone
useful as a pharmaceutical intermediate with high selectivity and, furthermore,
produces a product at 83 to 91% asymmetry yield if a catalyst precursor
is used in the presence of a co-oxidant. This selectivity is the highest
level as the hypervalent iodine catalyst technology.
- Spirolactones of high optical purity are obtained with a catalytic amount.
- Hypervalent iodine is generated in a reaction system by meta-chloroperbenzoic
2. Examples of reaction
- M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. Int. Ed. 2010, 49, 2175.
- M. Uyanik, T. Yasui, K. Ishihara, Tetrahedron 2010, 66, 5841.
- T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka,
S. B. Caemmerer, Y. Kita, Angew. Chem. Int. Ed. 2008, 47, 3787.
||Wako Catalog No.
||for Organic Synthesis
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