4-亚甲基- l -谷氨酸及其环丙基类似物的高效合成

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 1994-05-01 DOI:10.1016/S0957-4166(00)86244-8

Jesús Eacquerra, Concepión Pedregal ∗, Irene Micó, Carmen Nájera ∗

引用次数: 30

摘要

4-亚甲基- l -谷氨酸(1)和它的环丙基类似物2分别由n -氨基焦谷氨酸乙酯(3)经过2步和3步得到。以内酰胺烯酸锂与Eschenmoser盐为原料，制备了关键中间体n - boc -4-亚甲基戊氨酸乙酯(4)。以(S)-2-(叔丁基)-3-甲基-4-咪唑烷酮(7)为原料，三步制得环丙基衍生物2。中间体9是由烯酸锂7与丙烯酸丁酯(2-甲苯基甲基)(8)的非对映选择性反应得到的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Efficient synthesis of 4-methylene-L-glutamic acid and its cyclopropyl analogue

4-Methylene-L-glutamic acid (1) and its cyclopropyl analogue 2 were obtained from ethyl N-Bocpyroglutamate (3) in 2 and 3 steps, respectively. The key intermediate, ethyl N-Boc-4-methylenepyroglutamate (4) was prepared by reaction of tbe lithium lactam enolate with Eschenmoser's salt. Cyclopropyl derivative 2 was also prepared from (S)-2-(tert-butyl)-3-methyl-4-imidazolidinone (7) in 3 steps. The intermediate 9 was obtained by diastereoselective reaction of the lithium enolate of 7 with butyl (2-tosylmethyl)acrylate (8).

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.