A Biocatalytic Approach to Synthesizing Optically Active Orthogonally Protected trans-Cyclopentane-1,2-Diamine Derivatives

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• 作者：Javier Gonz&aacute ; lez-Sabí ; n ; Vicente Gotor ; Francisca Rebolledo
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：February 16, 2007
• 年：2007
• 卷：72
• 期：4
• 页码：1309 - 1314
• 全文大小：139K
• 年卷期：v.72,no.4(February 16, 2007)
• ISSN：1520-6904

文摘

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A straightforward chemoenzymatic synthesis of optically active trans-N,N-dialkylcyclopentane-1,2-diamines has been efficiently developed starting out from their analogous (±)-trans-2-(N,N-dialkylamino)cyclopentanols. The route involves the one-pot stereospecific transformation of the racemic amino alcoholsinto racemic diamines and a subsequent kinetic resolution by means of lipase-B from Candida antarctica-catalyzed acylation reactions. The careful selection of both the alkyl substituents present in the diamineand the derivatization strategy applied to the enzymatic reaction enabled the easy preparation of othersynthetically valuable optically active trans-cyclopentane-1,2-diamines derivatives.