Sripragna Burugupalli, Yupu Qiao, Allan D. Headley
{"title":"苯氧乙醛对硝基烯烃加成反应的高对映选择性有机催化","authors":"Sripragna Burugupalli, Yupu Qiao, Allan D. Headley","doi":"10.1016/j.tetasy.2017.09.018","DOIUrl":null,"url":null,"abstract":"<div><p>A novel category of di(<em>N</em>,<em>N</em><span>-dimethylbenzylamine)prolinol silyl ether<span><span> catalyst, which when used in conjunction with an acidic co-catalyst, generates an ammonium salt<span> supported organocatalyst<span><span>. This catalytic system is shown to be very effective for the Michael reaction of benzyloxyacetaldehyde and various nitroolefins in </span>isopropanol<span>. Excellent enantioselectivities (up to 99%) and </span></span></span></span>diastereoselectivities (</span></span><em>syn</em>/<em>anti</em> of 75:25) and short reaction times were obtained. The presence of the bulky OTMS group combined with the presence of two large <em>N</em>,<em>N</em><span>-dimethylbenzyl ammonium ion groups accounts for the effectiveness of this catalytic system.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1608-1611"},"PeriodicalIF":0.0000,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.09.018","citationCount":"1","resultStr":"{\"title\":\"Highly enantioselective organocatalysis of the Michael addition of benzyloxyacetaldehyde to nitroolefins\",\"authors\":\"Sripragna Burugupalli, Yupu Qiao, Allan D. Headley\",\"doi\":\"10.1016/j.tetasy.2017.09.018\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A novel category of di(<em>N</em>,<em>N</em><span>-dimethylbenzylamine)prolinol silyl ether<span><span> catalyst, which when used in conjunction with an acidic co-catalyst, generates an ammonium salt<span> supported organocatalyst<span><span>. This catalytic system is shown to be very effective for the Michael reaction of benzyloxyacetaldehyde and various nitroolefins in </span>isopropanol<span>. Excellent enantioselectivities (up to 99%) and </span></span></span></span>diastereoselectivities (</span></span><em>syn</em>/<em>anti</em> of 75:25) and short reaction times were obtained. The presence of the bulky OTMS group combined with the presence of two large <em>N</em>,<em>N</em><span>-dimethylbenzyl ammonium ion groups accounts for the effectiveness of this catalytic system.</span></p></div>\",\"PeriodicalId\":22237,\"journal\":{\"name\":\"Tetrahedron, asymmetry\",\"volume\":\"28 11\",\"pages\":\"Pages 1608-1611\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2017-11-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.09.018\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron, asymmetry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0957416617303518\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Chemistry\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron, asymmetry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0957416617303518","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Chemistry","Score":null,"Total":0}
Highly enantioselective organocatalysis of the Michael addition of benzyloxyacetaldehyde to nitroolefins
A novel category of di(N,N-dimethylbenzylamine)prolinol silyl ether catalyst, which when used in conjunction with an acidic co-catalyst, generates an ammonium salt supported organocatalyst. This catalytic system is shown to be very effective for the Michael reaction of benzyloxyacetaldehyde and various nitroolefins in isopropanol. Excellent enantioselectivities (up to 99%) and diastereoselectivities (syn/anti of 75:25) and short reaction times were obtained. The presence of the bulky OTMS group combined with the presence of two large N,N-dimethylbenzyl ammonium ion groups accounts for the effectiveness of this catalytic system.
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.
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