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首页> 外文会议>Asymmetric synthesis and application of α-amino acids >Synthesis and Application of Chiral α-Amino Acids by Kinetic Resolution of Urethane-Protected α-Amino Acid N-Carboxyanhydrides with Modified Cinchona Alkaloid Catalysts
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Synthesis and Application of Chiral α-Amino Acids by Kinetic Resolution of Urethane-Protected α-Amino Acid N-Carboxyanhydrides with Modified Cinchona Alkaloid Catalysts

机译：改性金鸡纳生物碱催化剂动力学拆分氨基甲酸酯保护的α-氨基酸N-羧酸酐合成手性α-氨基酸及其应用

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摘要

A general and efficient kinetic resolution of urethane-protected a-amino acid N-carboxyanhydrides (UNCA) that generates highly enantiomerically enriched a-amino acid derivatives in excellent yields is developed. Numerous UNCAs with different N-carbamoyl protecting groups and with a wide range of α-alkyl, α-aryl as well as α-alkenyl side chains are resolved with enzyme-like efficiency via this strategy. This modified cinchona alkaloid-catalyzed kinetic resolution of UNCA via alcoholysis provides a versatile and reliable route to optically active amino acid derivatives that are suitably protected for further synthetic elaborations. The reaction utilizes readily accessible substrates, cheap reagents, commercially available and fully recyclable catalysts and simple experimental protocols. These characteristics of the reaction render it a highly efficient, flexible and practical method for the asymmetric synthesis of a-amino acids. The further successful improvement of this cinchona alkaloid-catalyzed alcoholysis into a practical tool for large scale synthesis is made possible through the development of new and easily accessible cinchona alkaloid-based catalysts. The practical utility of thisrnnew resolution method for large scale synthesis is highlighted in a multi kilogram scale asymmetric synthesis of pro-pargylglycine, an unnatural amino acid that is a useful pharmaceutical intermediate but difficult to prepare using metal-catalyzed asymmetric hydrogenation of dehydro-amino acids.
机译：开发了氨基甲酸酯保护的α-氨基酸N-羧基酸酐（UNCA）的一般有效的动力学拆分方法，该化合物可产生高对映体富集的α-氨基酸衍生物，且产率极高。通过这种策略，可以以类似酶的效率拆分具有不同N-氨基甲酰基保护基团和广泛范围的α-烷基，α-芳基以及α-烯基侧链的许多UNCA。经由醇解的这种改进的金鸡纳生物碱催化的UNCA动力学拆分为光学活性的氨基酸衍生物提供了广泛而可靠的途径，该衍生物被适当地保护以用于进一步的合成修饰。该反应利用容易获得的底物，廉价的试剂，可商购的和可完全再循环的催化剂以及简单的实验方案。反应的这些特征使其成为α-氨基酸不对称合成的高效，灵活和实用的方法。通过开发新的且易于获得的基于金鸡纳生物碱的催化剂，可以将该金鸡纳生物碱催化的醇解进一步成功地改进为用于大规模合成的实用工具。这种新的拆分方法用于大规模合成的实际实用性在前公斤级甘氨酸的多公斤级不对称合成中得到了强调，前天然型甘氨酸是一种有用的药物中间体，但是很难用金属催化的脱氢氨基酸的不对称加氢制备。

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  • 会议地点 Chicago IL(US);Chicago IL(US)
  • 作者

    Jianfeng Hang; Yutaka Ishii; Yoshiro Furukawa; Li Deng;

  • 作者单位

    Department of Chemistry, Brandeis University,Waltham, MA 02454-9110;

    Research Laboratories, Daiso Company, Ltd., 9-Otakasu-cho,Amagasaki-shi 660-0842, Japan;

    Research Laboratories, Daiso Company, Ltd., 9-Otakasu-cho,Amagasaki-shi 660-0842, Japan;

    Department of Chemistry, Brandeis University,Waltham, MA 02454-9110;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 氨基酸;
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