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Stereoselective Synthesis of cis- and trans-Beta,Gamma-Unsaturated Carboxylic Esters via Reaction of Alkenyldichloroboranes with Ethyl Diazoacetate.

机译：通过烯基二氯硼烷与重氮基乙酸乙酯反应立体选择性合成顺式和反式β，γ-不饱和羧酸酯。

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摘要

Trans-Alkenyldichloroboranes, easily prepared by the reaction of dichloroborane-dimethyl sulfide complex with various alkynes in the presence of boron trichloride, react smoothly with ethyl diazoacetate at -65 C with the liberation of nitrogen. Treatment of the intermediates with methanol-water produces trans-Beta, gamma-unsaturated carboxylic esters stereoselectively in good yields. Similar treatment of cis-alkenyldichloroboranes provides the corresponding cis-Beta, gamma unsaturated esters.

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Brown, H. C.; Salunkhe, A. M.;
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年度 1991
页码 1-9
总页数 9
原文格式 PDF
正文语种 eng
中图分类工业技术;
关键词
Alkynes; Boron; Chlorides; Synthesis; Stereoselective synthesis; Cis- and trans-Alkenyldichloroboranes; Beta; High isomeric purity; Gamma-Unsaturated esters;

机译：炔烃;硼;氯化物;合成;立体选择性合成;顺式 - 和反式 - 烯基二氯硼烷;β;高异构体纯度;γ-不饱和酯;

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机译：I（II）碘化物介导的醛与γ，δ-叠氮基-α，β-不饱和酯的立体选择性合成δ-氨基-β'-羟基-β，γ-不饱和酯
2. Enantio- and diastereoselective synthesis of syn -β-hydroxy-α- vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-tms-9-borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway [J] . Kister J., Ess D.H., Roush W.R. Organic letters . 2013,第21期

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3. Enantio- and diastereoselective synthesis of syn -β-hydroxy-α- vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-tms-9-borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway [J] . Kister J., Ess D.H., Roush W.R. Organic letters . 2013,第21期

机译：通过烯丙基羧酸乙酯与10-tms-9-硼环[3.3.2]癸烷的还原性醛醇缩合反应进行对映和非对映选择性合成顺式-β-羟基-α-乙烯基羧酸酯，并进行了硼氢化反应的DFT分析
4. Multistep Microwave-Assisted Solvent-Free Organic Reactions: Synthesis of 1,6-Disubstituted-4-Oxo-1,4-Dihydro-Pyridine-3-Carboxylic Acid Benzyl Esters [C] . Mauro Panunzio, Maria Antonietta Lentini, Eileen Campana, International Conference on Microwave and High Frequency Heating . 2006

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机译：2,3- alenenoates在碱存在下与TsnBr2的反应：（1E，2E）-3-溴-4-氧代 - N-甲苯胺-2-链烷酰基氧基甲酰嘧啶酸乙酯乙酯的容易高度立体化合成

Stereoselective Synthesis of cis- and trans-Beta,Gamma-Unsaturated Carboxylic Esters via Reaction of Alkenyldichloroboranes with Ethyl Diazoacetate.

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