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| 顺式-和反式-2,5-二取代四氢呋喃的立体选择性合成 | |
| 引用本文： | 史鸿鑫,刘化章,Bloch R,Mandville G,林辉.顺式-和反式-2,5-二取代四氢呋喃的立体选择性合成[J].高等学校化学学报,2003,24(5):831-836. |
| 作者姓名： | 史鸿鑫 刘化章 Bloch R Mandville G 林辉 |
| 作者单位： | 1. 浙江工业大学化工学院,杭州,310032 2. Université de Paris-Sud,ICMO. 91405 Orsay Cédex,France 3. 浙江大学理学院化学系,杭州,310012 |
| 基金项目： | 中法政府科技合作课题(批准号:1996-4)资助 |
| 摘 要： | 内酯与有机锂试剂发生亲核加成反应,再在酸催化下用NaBH3CN还原,反应的立体选择性可能是由氢负离子在中间体氧鎓离子位阻最小的一侧进攻所引起.所得的三环化合物经热分解和加氢反应,制备顺式和反式-2,5-二取代四氢呋喃. |
| 关 键 词： | 立体选择性 氧杂环 二取代四氢呋喃 手性 |
| 文章编号： | 0251-0790(2003)05-0831-06 |
| 收稿时间： | 2002-04-30 |
Stereoselective Synthesis of cis- and trans-2,5-Disubstituted Tetrahydrofurans |
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| Bloch R,Mandville G.Stereoselective Synthesis of cis- and trans-2,5-Disubstituted Tetrahydrofurans[J].Chemical Research In Chinese Universities,2003,24(5):831-836. | |
| Authors: | Bloch R Mandville G |
| Institution: | 1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China; 2. Universite de Paris-Sud, ICMO 91405, Orsay Cedex, France; 3. Department of Chemistry, Institute of Science, Zhejiang University, Hangzhou 310012, China |
| Abstract: | A general route to either cis- or trans -2,5-disubstituted tetrahydrofurans was described by using the nucleophilic addition of organolithium derivatives to tricyclic lactones, followed by a highly stereocon-trolled acid-assisted reduction with sodium cyanoborohydride of the hemiketals formed. The stereoselec-tivity observed can be rationalized by the preferential approach of the hydride on the less hindered face of an oxonium ion intermediate. The cis- or trans-2, 5-disubstituted tetrahydrofurans were provided by the hot decomposition and then hydrogenation of tricycle compounds produced. |
| Keywords: | Stereoselectivity Oxygen heterocycles Disubstituted tetrahydrofuran Chirality |
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