| DiastereoselectiveandEnantioselectiveSynthesisof(1S,2S)-2-Ethyl-1-aminocyclopropaneCarboxylicAcid |
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| 引用本文： | Yi Bo ZHOU,Jun An MA,Li Xin WANG,Qi Lin ZHOU* State Key Laboratoratory and Institute of Elemento-Organic Chemistry,Nankai University Tianjin 300071. DiastereoselectiveandEnantioselectiveSynthesisof(1S,2S)-2-Ethyl-1-aminocyclopropaneCarboxylicAcid[J]. 中国化学快报, 2002, 13(10) |
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| 作者姓名： | Yi Bo ZHOU Jun An MA Li Xin WANG Qi Lin ZHOU* State Key Laboratoratory and Institute of Elemento-Organic Chemistry Nankai University Tianjin 300071 |
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| 作者单位： | Yi Bo ZHOU，Jun An MA，Li Xin WANG，Qi Lin ZHOU* State Key Laboratoratory and Institute of Elemento-Organic Chemistry，Nankai University Tianjin 300071 |
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| 基金项目： | 国家自然科学基金，financial support |
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| 摘 要： | During the last decade, 1-aminocyclopropanecarboxylic acid and its derivatives (ACCS) have attracted increasing attention of organic and bioorganic chemists due to their outstanding biological properties, ranging from antimicrobial, insecticidal, plant growth and fruit ripening controls, etc.1. Moreover, the three-membered carbocycle provides building blocks of unprecedented synthetic potential because it undergoes selective ring opening, ring enlargement or cycloaddition reactions2. The mo…
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Diastereoselective and Enantioselective Synthesis of (1S, 2S)-2- Ethyl-1-aminocyclopropane Carboxylic Acid |
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| Yi Bo ZHOU,Jun An MA,Li Xin WANG,Qi Lin ZHOU. Diastereoselective and Enantioselective Synthesis of (1S, 2S)-2- Ethyl-1-aminocyclopropane Carboxylic Acid[J]. Chinese Chemical Letters, 2002, 13(10) |
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| Authors: | Yi Bo ZHOU Jun An MA Li Xin WANG Qi Lin ZHOU |
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| Affiliation: | State Key Laboratoratory and Institute of Elemento-Organic Chemistry, Nankai UniversityTianjin 300071 State Key Laboratoratory and Institute of Elemento-Organic Chemistry, Nankai UniversityTianjin 300071 State Key Laboratoratory and Institute of Elemento-Organic Chemistry, Nankai UniversityTianjin 300071 State Key Laboratoratory and Institute of Elemento-Organic Chemistry, Nankai UniversityTianjin 300071 |
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| Abstract: | Pd(0) Complex prepared from Pd(dba)2 and chiral quinolinyl-oxazoline ligand can catalyze alkylation and cyclization reaction of 1, 4-dichlorobut-2-ene 1 with anion of N-(di- phenylmethylene)amino acetonitrile 2 to provide (E)-2-ethenyl-1-N-(diphenylmethylene) amino cyclopropane carbonitrile 3 with 100% de and 20% ee. Reduction of (E)-3 by diimide followed by acidic hydrolysis afforded (1S, 2S)-2-ethyl-1-aminocyclopropanecarboxylic acid 9, a natural product coronamic acid. |
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| Keywords: | Chiral Pd catalyst quinolinyl-oxazoline cyclopropanecarboxylic acid. |
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