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Chiral Hypervalent Iodine

(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.



    INDEX
  1. Features

  2. Examples of reaction

  3. Related products (4-Pyridineboronic Acid Catalysts)

  4. Wako's Green Chemistry Products
1. Features

  • Spirolactones of high optical purity are obtained with a catalytic amount.
  • Hypervalent iodine is generated in a reaction system by meta-chloroperbenzoic acid.

2. Examples of reaction


References
  1. M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. Int. Ed. 2010, 49, 2175.
  2. M. Uyanik, T. Yasui, K. Ishihara, Tetrahedron 2010, 66, 5841.
  3. T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, Y. Kita, Angew. Chem. Int. Ed. 2008, 47, 3787.
Product Name Grade Package Size Wako Catalog No.
(2R,2R')-2,2'-(2-Iodo-1,3-phenylene)bis(oxy)bis(N-mesitylpropanaamide) for Organic Synthesis 250 mg 095-06051
1 g 091-06053

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3. Related products
4-Pyridineboronic Acid Catalysts
⇒ Use as a dehydrative condensation agent gives amides from an equimolar mixture of carboxylic acids and amines!

4. Wako's Green Chemistry Products
Wako Product Update < Organic - No.1 > (2.82 MB/16p)




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