Synthesis and Application of Chiral a-Amino Acidsby Kinetic Resolution of Urethane-Protected a-AminoAcid N-Carboxyanhydrides with Modified CinchonaAlkaloid Catalysts

机译：用改性的CinchonaHalid催化剂对氨基甲酸酯保护的A-氨基酸N-羧酸酐的动力学分辨率的合成与应用

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A general and efficient kinetic resolution of urethane-protecteda-amino acid N-carboxyanhydrides (UNCA) that generateshighly enantiomerically enriched a-amino acid derivatives inexcellent yields is developed. Numerous UNCAs withdifferent N-carbamoyl protecting groups and with a wide rangeof a-alkyl, a-aryl as well as a-alkenyl side chains are resolvedwith enzyme-like efficiency via this strategy. This modifiedcinchona alkaloid-catalyzed kinetic resolution of UNCA viaalcoholysis provides a versatile and reliable route to opticallyactive amino acid derivatives that are suitably protected forfurther synthetic elaborations. The reaction utilizes readilyaccessible substrates, cheap reagents, commercially availableand fully recyclable catalysts and simple experimentalprotocols. These characteristics of the reaction render it ahighly efficient, flexible and practical method for theasymmetric synthesis of a-amino acids. The further successfulimprovement of this cinchona alkaloid-catalyzed alcoholysisinto a practical tool for large scale synthesis is made possiblethrough the development of new and easily accessiblecinchona alkaloid-based catalysts. The practical utility of this.

机译：开发了一种氨基甲酸酯保护的氨基酸正氨基酸正氨基酸N-羧酰酐（UNCA）的一般和高效的动力学分辨率，产生了不可缩放的α-氨基酸衍生物。许多不加入的N-氨基甲酰基保护基团和烷基，α-芳基以及A-链烯基侧链的宽范围是通过该策略的酶样效率解决。这种UNCA基团的改性菌胰岛碱催化剂催化的动力学分辨率提供了与光学氨基酸衍生物的多功能和可靠的途径，该途径适当地保护用于合成阐述。该反应利用真正可接为的底物，廉价试剂，商业上可用的全新可回收催化剂和简单的实验性协议。这些反应的这些特征使其成为α对称合成α-氨基酸的高效，灵活和实用的方法。这种CinChona生物碱催化醇解的进一步成功的甲醇分析是用于大规模合成的实用工具，使得具有新的且易于探测的途径生物碱基催化剂的开发。这个实用的效用。

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《ACS symposium asymmetric synthesis and application of α-amino acids》|2009年||共23页
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Jianfeng Hang; Yutaka Ishii; Yoshiro Furukawa; Li Deng;
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中图分类氨基酸;
关键词
Synthesis; Application; Chiral a-Amino Acids;

机译：合成;应用;手性A-氨基酸;

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1. Practical syntheses of chiral alpha-amino acids and chiral half-esters by kinetic resolution of urethane-protected alpha-amino acid N-carboxyanhydrides and desymmetrization of cyclic meso-anhydrides with new modified cinchona alkaloid catalysts [J] . Ishii Y, Fujimoto R, Mikami M, Organic process research & development . 2007,第3期

机译：通过氨基甲酸酯保护的α-氨基酸N-羧基酐的动力学拆分和环状介孔酸酐的不对称化与新型改性金鸡纳生物碱催化剂的实用合成手性α-氨基酸和手性半酯
2. Chiral Bicyclie Imidazole Nucleophilic Catalysts: Design, Synthesis, and Application to the Kinetic Resolution of Arylalkylcarbinols [J] . Zhenfeng Zhang, Mo Wang, Fang Xie Advanced synthesis & catalysis . 2014,第14a15期

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3. A new cost-effective Ru-chloramphenicol base derivative catalyst for the asymmetric transfer hydrogenation/dynamic kinetic resolution of N-Boc alpha-amino-beta-ketoesters and its application to the synthesis of the chiral core of vancomycin [J] . Wang Xinlong, Xu Lingjun, Xiong Fangjun, RSC Advances . 2016,第44期

机译：一种新的经济高效的Ru-氯霉素基础衍生物基础衍生物，用于N-BOCα-氨基-β-酮酯的不对称转移氢化/动态动力学分辨率及其在万古霉素的手性核心合成中的应用
4. Synthesis and Application of Chiral a-Amino Acidsby Kinetic Resolution of Urethane-Protected a-AminoAcid N-Carboxyanhydrides with Modified CinchonaAlkaloid Catalysts [C] . Jianfeng Hang, Yutaka Ishii, Yoshiro Furukawa, ACS symposium asymmetric synthesis and application of α-amino acids . 2009

机译：用改性的CinchonaHalid催化剂对氨基甲酸酯保护的A-氨基酸N-羧酸酐的动力学分辨率的合成与应用
5. Chiral nucleophilic catalysts: Applications in the synthesis of 3,3-disubstituted oxindoles and parallel kinetic resolution [D] . Duffey, Trisha Ann 2008

机译：手性亲核催化剂：在3,3-二取代的羟吲哚的合成中的应用和平行动力学拆分
6. Design and Stereoselective Preparation of a New Class of Chiral Olefin Metathesis Catalysts and Application to Enantioselective Synthesis of Quebrachamine: Catalyst Development Inspired by Natural Product Synthesis [O] . Elizabeth S. Sattely, Simon J. Meek, Steven J. Malcolmson, -1

机译：新型手性烯烃复分解催化剂的设计和立体选择性制备及其在Quebrachamine对映选择性合成中的应用：天然产物合成的启发
7. Development of a Recyclable Fluorous Chiral Phase-Transfer Catalyst: Application to the Catalytic Asymmetric Synthesis of a-Amino Acids [O] . -1

机译：可再循环荧光手性相转移催化剂的研制：在催化不对称合成A-氨基酸的应用

Synthesis and Application of Chiral a-Amino Acidsby Kinetic Resolution of Urethane-Protected a-AminoAcid N-Carboxyanhydrides with Modified CinchonaAlkaloid Catalysts

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