New Organometallic Synthesis Method Using Metallic Strontium
Cupertino, CA, October 19, 2012 --(PR.com)-- Fuji Molecular Planning (Kanazawa-ku, Yokohama, Japan) is commercializing a new organometallic synthesis method utilizing metallic Strontium (Sr) developed by Dr. Norikazu Miyoshi at the University of Tokushima in Japan.
The Sr-mediated reaction produces high yields of both akylated and dialkylated adducts using alkyl halides with easy handling. This represents an improvement on the well-established Grignard method for diaklylations of esters using metallic magnesium and alkyl halides. The Grignard reaction often produces unwanted side reactions. For example, in the reaction of methyl benzoate and three equivalents of isopropyl Grignard reagent, the desired diaklylated adduct yield was 32%. Compare this with the 96% yield obtained using metallic Strontium and 1-Iodo-2-methylpropane under the same reaction conditions.
Similarly, the Sr-mediated esterification was used successfully with bulky tert-alcohols with carboxylic acid derivatives. Esterification of secondary and tertiary alcohols is notoriously difficult but they are fundamental organic synthesis reactions. The Sr-mediated approach addresses these challenges and offers a high-yield solution.
Dr. Miyoshi’s group has previously reported the successful use of metallic strontium to obtain high yields in the alkylation of aldehydes or imines with alkyl iodides1,2 and dialkylation of esters with alkyl iodides3.
Fuji Molecular Planning (http://chiral.ktpc.or.jp/index_engl.htm) is a research-based company specializing in the organic synthesis of chiral compounds and have developed new synthetic methods important in the pharmaceutical, agrochemical, and electronic fields.
For additional information about this technology or licensing this technology, please contact the Tokushima University Silicon Valley Office at hq@b-bridge.com.
References
1. N. Miyoshi, K. Kamiura, H. Oka, A. Kita, R. Kuwata, D. Ikehara, M. Wada, Bull. Chem. Soc. Jpn., 2004, 77, 341.
2. N. Miyoshi, D. Ikehara, T. Kohno, A. Matsui, M. Wada, Chem. Lett. 2005, 34,760.
3. N. Miyoshi, T. Matsuo, M. Wada, Euro. J. Org. Chem., 2005, 4253.
The Sr-mediated reaction produces high yields of both akylated and dialkylated adducts using alkyl halides with easy handling. This represents an improvement on the well-established Grignard method for diaklylations of esters using metallic magnesium and alkyl halides. The Grignard reaction often produces unwanted side reactions. For example, in the reaction of methyl benzoate and three equivalents of isopropyl Grignard reagent, the desired diaklylated adduct yield was 32%. Compare this with the 96% yield obtained using metallic Strontium and 1-Iodo-2-methylpropane under the same reaction conditions.
Similarly, the Sr-mediated esterification was used successfully with bulky tert-alcohols with carboxylic acid derivatives. Esterification of secondary and tertiary alcohols is notoriously difficult but they are fundamental organic synthesis reactions. The Sr-mediated approach addresses these challenges and offers a high-yield solution.
Dr. Miyoshi’s group has previously reported the successful use of metallic strontium to obtain high yields in the alkylation of aldehydes or imines with alkyl iodides1,2 and dialkylation of esters with alkyl iodides3.
Fuji Molecular Planning (http://chiral.ktpc.or.jp/index_engl.htm) is a research-based company specializing in the organic synthesis of chiral compounds and have developed new synthetic methods important in the pharmaceutical, agrochemical, and electronic fields.
For additional information about this technology or licensing this technology, please contact the Tokushima University Silicon Valley Office at hq@b-bridge.com.
References
1. N. Miyoshi, K. Kamiura, H. Oka, A. Kita, R. Kuwata, D. Ikehara, M. Wada, Bull. Chem. Soc. Jpn., 2004, 77, 341.
2. N. Miyoshi, D. Ikehara, T. Kohno, A. Matsui, M. Wada, Chem. Lett. 2005, 34,760.
3. N. Miyoshi, T. Matsuo, M. Wada, Euro. J. Org. Chem., 2005, 4253.
Contact
The University of Tokushima / B-Bridge International, Inc.
Mie Tamaki
408-252-6200
Mie Tamaki
408-252-6200
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