Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products

Makoto Shimizu; Miki Mushika; Isao Mizota; Yusong Zhu

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Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products

机译：亚氨基丙二酸酯的双亲核加成，导致季α-氨基二酯的合成和产物的脱对称化

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Alkylation of iminomalonate with Grignard reagents followed by oxidation and allylation gave symmetrical quaternary α-amino diesters in good yields. Subsequent desymmetrization of a diol derivative from these products was conducted via asymmetric carbamylation catalyzed by Cu-Bnbox to give chiral quaternary aminodiol mono-carbamates.

机译：亚氨基丙二酸酯用格氏试剂烷基化，然后氧化和烯丙基化，得到对称的季铵α-氨基二酯，收率很高。随后通过Cu-Bnbox催化的不对称氨甲酰化作用，使这些产物中的二醇衍生物脱对称，得到手性季氨基二醇单氨基甲酸酯。

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《RSC Advances》 |2019年第40期|共8页
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Makoto Shimizu; Miki Mushika; Isao Mizota; Yusong Zhu;
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中图分类化学;
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1. Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary alpha-amino diesters and desymmetrization of the products [J] . Shimizu Makoto, Mushika Miki, Mizota Isao, RSC Advances . 2019,第40期

机译：二核外核酸产物，导致季甲氨基二酯的合成和产品的脱差异化
2. Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products [J] . Makoto Shimizu, Miki Mushika, Isao Mizota, RSC Advances . 2019,第40期

机译：亚氨基丙二酸酯的双亲核加成，导致季α-氨基二酯的合成和产物的脱对称化
3. Enantioselective Synthesis of r-Quaternary Amino Acid Derivatives by Sequential Enzymatic Desymmetrization and Curtius Rearrangement of r,r-Disubstituted Malonate Diesters [J] . Violeta Iosub, Anton R. Haberl, Jennifer Leung, The Journal of Organic Chemistry . 2010,第5期

机译：r，r-二取代的丙二酸酯二酸酯的顺序酶促不对称化和Curtius重排对映体合成r-季氨基酸衍生物
4. Michael Addition Reactions between Nucleophilic GlycineEquivalents and Acrylic Acid Derivatives as a Practicaland Generalized Approach to the Asymmetric Synthesisof II-Substituted-a-Amino Acids [C] . Vadim A. Soloshonok, Hisanori Ueki, Trevor K. Ellis ACS symposium asymmetric synthesis and application of α-amino acids . 2009

机译：亲核糖糖糖尿剂与丙烯酸衍生物之间的迈克尔添加反应作为不对称合成的不对称 - A-氨基酸的不对称方法的普遍化方法
5. PART I. ON THE STEREOCHEMISTRY OF THE ROBINSON-SCHOPF REACTION. A STEREOSPECIFIC TOTAL SYNTHESIS OF THE LADYBUG DEFENSE ALKALOIDS PRECOCCINELLINE AND COCCINELLINE. PART II. STUDIES ON THE STEREOCHEMISTRY OF NUCLEOPHILIC ADDITIONS TO DELTA(1)-PIPERIDEINIUM SALTS. A STEREOSPECIFIC TOTAL SYNTHESIS OF D,L-MONOMORINE I - THE TRAIL PHEROMONE OF THE PHARAOH ANT, AND A STEREOSPECIFIC SYNTHESIS OF ONE OF THE STEREOISOMERS OF GEPHYROTOXIN 223 [D] . LEE, ALBERT WAI MING 1980

机译：第一部分：鲁宾逊-肖普夫反应的立体化学。瓢虫防御碱生物碱和可可碱的立体比总合成。第二部分δ（1）-哌啶盐的核亲酸加成物的立体化学研究。 D，L-单鸟嘌呤I的立体异构体的全合成-对位蚂蚁的轨迹信息素，以及一种细菌毒素的立体异构体223
6. Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines [O] . Hélène Pellissier 2018

机译：通过对映异构亚胺的对映选择性催化亲核加成反应合成手性3-取代的3-氨基-2-氧吲哚
7. Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products [O] . Makoto Shimizu, Miki Mushika, Isao Mizota, 2019

机译：二核外核酸产物，导致季α-氨基二酯的合成和产物的脱差异化

Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products

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