A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis

Sarabia F.; Vivar-García C.; García-Castro M.; García-Ruiz C.; Martín-Gálvez F.; Sánchez-Ruiz A.; Chammaa S.

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A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis

机译：基于一类新的手性salts盐的高立体选择性的缩水甘油酰胺合成：在不对称合成中的应用

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A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98 %). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.

机译：由α-氨基酸设计并合成了一种新型的以双环体系为特征的手性sulf盐。通过对treatment盐进行碱性处理而制备的它们相应的酰基化物，可与各种简单的手性醛平稳反应，以合理，非常好的收率和出色的立体选择性（> 98％）提供反式环氧酰胺。发现获得的环氧酰胺可用作合成构件。因此，它们被还原成其相应的环氧醇，并与不同类型的亲核试剂进行环氧乙烷开环反应。

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《Chemistry: A European journal》 |2012年第47期|共12页
作者
Sarabia F.; Vivar-García C.; García-Castro M.; García-Ruiz C.; Martín-Gálvez F.; Sánchez-Ruiz A.; Chammaa S.;
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正文语种 eng
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关键词
amides; asymmetric synthesis; natural products; oxiranes; ylides;

机译：酰胺;不对称合成;天然产物;环氧乙烷;乙酰胺;

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1. A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis [J] . Sarabia F., Vivar-García C., García-Castro M., Chemistry: A European journal . 2012,第47期

机译：基于一类新的手性salts盐的高立体选择性的缩水甘油酰胺合成：在不对称合成中的应用
2. Diastereoselective synthesis of aryl and alkyl trans-glycidic amides from pseudoephedrine-derived sulfonium salt. Chemospecific exo-tet ring closure for morpholin-3-ones [J] . Aparicio D.M., Gnecco D., Juárez J.R., Tetrahedron . 2012,第49期

机译：从伪麻黄碱衍生的sulf盐非对映选择性合成芳基和烷基反式缩水甘油酰胺。化学特异的exo-tet闭环用于吗啉-3-酮
3. Diastereoselective synthesis of aryl and alkyl trans-glycidic amides from pseudoephedrine-derived sulfonium salt. Chemospecific exo-tet ring closure for morpholin-3-ones [J] . Aparicio D.M., Gnecco D., Juárez J.R., Tetrahedron . 2012,第49期

机译：从伪麻黄碱衍生的sulf盐非对映选择性合成芳基和烷基反式缩水甘油酰胺。化学特异的exo-tet闭环用于吗啉-3-酮
4. A Synthesis of Newly Designed Polymer-supported Chiral Catalyst and Its Application to Highly Stereoselective Asymmetric Cyclopropanation Reactions [C] . A. Mohamed Abu-Elfotoh, Kesiny Phomkeona, Kazutaka Shibatomi Symposium on Organometallic Chemistry . 2008

机译：新设计的聚合物支持的手性催化剂的合成及其在高度立体选择性不对称环丙烷反应中的应用
5. Highly efficient asymmetric synthesis of novel diphosphine ligands with additional chiral centers on the backbone and their applications in asymmetric hydrogenation reactions. [D] . Qiu, Liqin. 2003

机译：在骨架上具有额外手性中心的新型二膦配体的高效不对称合成及其在不对称氢化反应中的应用。
6. Synthesis of Polymer-supported Chiral Lithium Amide Bases and Application in Asymmetric Deprotonation of Prochiral Cyclic Ketones [O] . Lili Ma, Paul G. Williard -1

机译：聚合物支撑的手性锂酰胺碱的合成及其在手性环酮不对称脱质子中的应用
7. Highly Enantioselective Synthesis of Glycidic Amides Using Camphor-Derived Sulfonium Salts. Mechanism and Applications in Synthesis [O] . -1

机译：使用樟脑衍生的锍盐高度对糖尿病酰胺的合成。合成机制和应用

A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis

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