Chemoenzymatic Dynamic Kinetic Resolution of Primary Amines Using a Recyclable Palladium Nanoparticle Catalyst Together with Lipases

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• 作者：Karl P. J. Gustafson ; Richard Lihammar ; Oscar Verho ; Karin Engstr枚m ; Jan-E. B盲ckvall
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：May 2, 2014
• 年：2014
• 卷：79
• 期：9
• 页码：3747-3751
• 全文大小：263K
• 年卷期：v.79,no.9(May 2, 2014)
• ISSN：1520-6904

文摘

A catalyst consisting of palladium nanoparticles supported on amino-functionalized siliceous mesocellular foam (Pd-AmP-MCF) was used in chemoenzymatic dynamic kinetic resolution (DKR) to convert primary amines to amides in high yields and excellent ee鈥檚. The efficiency of the nanocatalyst at temperatures below 70 掳C enables reaction conditions that are more suitable for enzymes. In the present study, this is exemplified by subjecting 1-phenylethylamine (1a) and analogous benzylic amines to DKR reactions using two commercially available lipases, Novozyme-435 (Candida antartica Lipase B) and Amano Lipase PS-C1 (lipase from Burkholderia cepacia) as biocatalysts. The latter enzyme has not previously been used in the DKR of amines because of its low stability at temperatures over 60 掳C. The viability of the heterogeneous Pd-AmP-MCF was further demonstrated in a recycling study, which shows that the catalyst can be reused up to five times.