Direct Synthesis of N-Hydroxy #beta#-Amino Acid Esters from Carboxylic Esters and Nitrones

Kazuhiro Kobayashi; Takeshi Matoba; Susumu Irisawa; Atsushi Takanohashi; Miyuki Tanmatsu; Osamu Morikawa; Hisatoshi Konishi

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Direct Synthesis of N-Hydroxy #beta#-Amino Acid Esters from Carboxylic Esters and Nitrones

机译：由羧酸酯和亚硝基直接合成N-羟基＃β＃-氨基酸酯

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The direct synthesis of the title amino acid derivatives from carboxylic esters and nitrones can be achieved in fair to good yields when lithium or magnesium ester enolates were treated with nitrones in THF at -78 deg C or in Et_2O at -20 to 0 deg C, respectively. The products from the reaction of t-butyl acetate with 3,4-dihydroisoquinoline N-oxide or 5,5-dimethylpyrroline 1-oxide were transformed into (1,2,3,4-tetrahydroisoquinolin-1-ylidene)acetate or (pyrrlidin-2-ylidene)acetate derivatives inthe presence of triphenylphosphine, carbon tetrachloride, and triethylamine in refluxing dichloromethane.

机译：当将锂或镁酯烯醇盐在THF中于-78℃或在Et_2O中于-20至0℃下用硝酮处理时，可以从羧酸酯和硝酮直接合成标题氨基酸衍生物，并且收率相当好。分别。将乙酸叔丁酯与3,4-二氢异喹啉N-氧化物或5,5-二甲基吡咯啉1-氧化物的反应产物转化为（1,2,3,4-四氢异喹啉-1-亚基）乙酸酯或（吡咯烷酮）在三苯基膦，四氯化碳和三乙胺的存在下，在回流的二氯甲烷中存在乙酸-2-亚苄基酯的衍生物。

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《Bulletin of the Chemical Society of Japan》 |2000年第12期|共5页
作者
Kazuhiro Kobayashi; Takeshi Matoba; Susumu Irisawa; Atsushi Takanohashi; Miyuki Tanmatsu; Osamu Morikawa; Hisatoshi Konishi;
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中图分类化学;化学工业;
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1. Direct Synthesis of N-Hydroxy #beta#-Amino Acid Esters from Carboxylic Esters and Nitrones [J] . Kazuhiro Kobayashi, Takeshi Matoba, Susumu Irisawa, Bulletin of the Chemical Society of Japan . 2000,第12期

机译：由羧酸酯和亚硝基直接合成N-羟基＃β＃-氨基酸酯
2. Flavouring Group Evaluation 62 Rev1 (FGE.62 Rev1): Consideration of of linear and branched‐chain aliphatic unsaturated, unconjugated alcohols, aldehydes, acids, and related esters evaluated by JECFA (61st and 68th meeting) structurally related to branched‐ and straight‐chain unsaturated carboxylic acids and esters of these with aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2 (2010) and to straight‐ and branched‐chain aliphatic unsaturated primary alcohols, aldehydes, carboxylic acids, and esters evaluated by EFSA in FGE.06Rev1 (2008) [J] . EFSA Journal . 2010,第11期

机译：香精基团评估报告62 Rev1（FGE.62 Rev1）：考虑了由JECFA评估的直链和支链脂族不饱和，未共轭的醇，醛，酸和相关酯（61 st 和68
3. Synthesis and antimicrobial activity of new (4,4,4-trihalo-3-oxo-but-1-enyl)-carbamic acid ethyl esters, (4,4,4-trihalo-3-hydroxy-butyl)-carbamic acid ethyl esters, and 2-oxo-6-trihalomethyl-(1,3)oxazinane-3-carboxylic acid ethyl esters. [J] . Zanatta N, Borchhardt DM, Alves SH, Bioorganic and Medicinal Chemistry . 2006,第9期

机译：新的（4,4,4-三卤-3-氧代丁-1-烯基）氨基甲酸乙酯，（4,4,4-三卤-3-羟基丁基）-氨基甲酸乙酯的合成及抑菌活性酯和2-氧代-6-三卤代甲基-（1,3）恶嗪烷-3-羧酸乙酯。
4. Influence of Carboxylic Acid-Carboxylic Ester Ratio of Carboxylic Acid Ester Superplasticizer on Characteristics of Cement Mixtures [C] . G. Ferrari, T. Cerulli, P. Clemente, CANMET/ACI international conference on superplasticizers and other chemical admixtures in concrete . 2000

机译：羧酸酯高效减水剂的羧酸酯比对水泥混合料性能的影响
5. 1. Studies directed toward the synthesis of 20B-carbachaparrinone analogs via a samarium (II) iodide ring closure of a highly functionalized intermediate. 2. Synthesis of 5-oxo-cyclopent-1-enecarboxylic acid methyl esters via a novel tandem aldol-knoevenagel condensation. 3. Novel carbocyclic ring formation via intramolecular enol trapping of an allyl cation in acidic polar media. [D] . DeSelms, Robert Herschel. 2002

机译：1.研究针对通过高度官能化中间体的碘化sa（II）闭环合成20B-氨基苯甲酰吗啉酮类似物。 2.通过新型串联的羟醛-knoevenagel缩合合成5-氧代-环戊-1-烯羧酸甲酯。 3.通过在酸性极性介质中烯丙基阳离子的分子内烯醇捕获而形成新的碳环。
6. Scientific Opinion on Flavouring Group Evaluation 5 Revision 3 (FGE.05Rev3): Branched‐ and straight‐chain unsaturated aldehydes dienals unsaturated and saturated carboxylic acids and related esters with saturated and unsaturated aliphatic alcohols and a phenylacetic acid related ester from chemical groups 1 2 3 5 and 15 [O] . EFSA Food Additives and Flavourings (FAF), Maged Younes, Gabriele Aquilina, 2019

机译：关于调味剂基团评估5的科学意见修订版3（FGE.05Rev3）：支链和直链不饱和醛二烯不饱和和饱和羧酸及相关酯与饱和和不饱和脂族醇以及化学基团与苯乙酸有关的酯1、2、3、5和15
7. Synthesis of Allyl Ester of Prostaglandin E and the Conversion of the Allyl Ester Moiety into Carboxylic Acid by Chemical Method. A Highly Practical Synthesis of Natural PGE1and Limaprost [O] . Naoya Ono, Mie Tsuboi, Sentaro Okamoto, 1992

机译：用化学法将前列腺素E的烯丙基酯的合成及烯丙基酯部分将烯丙基酯部分转化为羧酸。天然PGE1和Limaprost的高实际合成

Direct Synthesis of N-Hydroxy #beta#-Amino Acid Esters from Carboxylic Esters and Nitrones

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