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Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles 小环化合物合成中的自由基多米诺反应:含环丙烷多环的多环化
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01276-2
Zorana Ferjančić, Živorad Čeković, Radomir N Saičić
{"title":"Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles","authors":"Zorana Ferjančić,&nbsp;Živorad Čeković,&nbsp;Radomir N Saičić","doi":"10.1016/S1387-1609(01)01276-2","DOIUrl":"10.1016/S1387-1609(01)01276-2","url":null,"abstract":"<div><p>Free radical approach to fused vinylcyclopropane derivatives is described. Homolytic decomposition of Barton esters <strong>4a–f</strong> in the presence of activated alkynes affords bicyclo〚3.1.0〛hex-2-ene derivatives <strong>5a–g</strong> in moderate yields (18–52 %). The propagation sequence comprises: intermolecular addition/5-<em>exo</em>-cyclization/3-<em>exo</em>-cyclization/β-elimination, and allows for a one-pot synthesis of bicyclic cyclopropane derivatives starting from two acyclic, unsaturated compounds.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 599-610"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01276-2","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84978507","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Highly diastereoselective radical addition–cyclization strategy: facile synthesis of substituted furans 高度非对映选择性自由基加成-环化策略:取代呋喃的简易合成
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01279-8
Mukund P. Sibi, Tara R. Rheault , Hideto Miyabe , Kalyani Patil, Craig P. Jasperse
{"title":"Highly diastereoselective radical addition–cyclization strategy: facile synthesis of substituted furans","authors":"Mukund P. Sibi,&nbsp;Tara R. Rheault ,&nbsp;Hideto Miyabe ,&nbsp;Kalyani Patil,&nbsp;Craig P. Jasperse","doi":"10.1016/S1387-1609(01)01279-8","DOIUrl":"10.1016/S1387-1609(01)01279-8","url":null,"abstract":"<div><p>A novel strategy is described in which an intermolecular carbon-centered radical addition to a β-oxygenated acceptor followed by intramolecular cyclization leads to the formation of 2,3,4- and 2,3,4,5-substituted furan rings. Excellent levels of 2,4-<em>trans</em> selectivity are observed in accordance with the Beckwith–Houk model for selectivity in 5-<em>exo</em> radical cyclizations.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 581-584"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01279-8","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81607665","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
α-Scission of sulfonyl radicals: a versatile process for organic synthesis α-磺基自由基的断裂:有机合成的通用过程
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01270-1
Frédérique Bertrand , Frédéric Le Guyader , Lucia Liguori , Gilles Ouvry , Béatrice Quiclet-Sire , Stéphanie Seguin , Samir Z. Zard
{"title":"α-Scission of sulfonyl radicals: a versatile process for organic synthesis","authors":"Frédérique Bertrand ,&nbsp;Frédéric Le Guyader ,&nbsp;Lucia Liguori ,&nbsp;Gilles Ouvry ,&nbsp;Béatrice Quiclet-Sire ,&nbsp;Stéphanie Seguin ,&nbsp;Samir Z. Zard","doi":"10.1016/S1387-1609(01)01270-1","DOIUrl":"10.1016/S1387-1609(01)01270-1","url":null,"abstract":"<div><p>The reversible addition of aliphatic radicals to sulphur dioxide can be exploited to design a variety of tin-free chain reactions. This brief review summarises some of the possibilities, namely radical allylation, vinylation, alkynylation, and azidation of various substrates.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 547-555"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01270-1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83976335","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 9
A cascade radical-mediated macrocyclisation–transannulation approach to oestrogen steroids 级联自由基介导的雌激素类固醇大环化-环化途径
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01271-3
Miguel Angel González Cardente, Stuart McCulloch, Gerald Pattenden
{"title":"A cascade radical-mediated macrocyclisation–transannulation approach to oestrogen steroids","authors":"Miguel Angel González Cardente,&nbsp;Stuart McCulloch,&nbsp;Gerald Pattenden","doi":"10.1016/S1387-1609(01)01271-3","DOIUrl":"10.1016/S1387-1609(01)01271-3","url":null,"abstract":"<div><p>A new approach to ring A aromatic steroids, based on cascade 13-<em>endo</em>-<em>trig/dig</em> macrocyclisations followed by sequential 5-<em>exo-trig</em> and 6-<em>exo-trig</em> transannulations, exemplified in the syntheses of the <em>cis,anti,trans</em> tetracycle <strong>9</strong> and the <em>trans,syn</em> tetracycle <strong>13</strong> from the <em>ortho</em>-substituted aryl polyen(yne) precursors, <strong>8</strong> and <strong>12</strong> respectively, is described.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 571-574"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01271-3","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88571467","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cyclisation of α-chiral aminyl radicals α-手性胺基自由基的环化
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01281-6
W Russell Bowman, Daniel R Coghlan, Hitesh Shah
{"title":"Cyclisation of α-chiral aminyl radicals","authors":"W Russell Bowman,&nbsp;Daniel R Coghlan,&nbsp;Hitesh Shah","doi":"10.1016/S1387-1609(01)01281-6","DOIUrl":"10.1016/S1387-1609(01)01281-6","url":null,"abstract":"<div><p>α-Chiral aminyl radicals have been generated from sulfenamides of α-amino acid esters and α-phenylethylamine using Bu<sub>3</sub>SnH. The aminyl radicals of α-amino acid esters undergo 5-<em>exo</em>-<em>trig</em> cyclisation reactions onto side chain alkenes to yield proline analogues with reasonable diastereoselectivity. Preliminary studies show urethanyl radicals generated from sulfenamides of alkenyl urethane derivatives of α-amino acid esters and α-phenylethylamine undergo 5-<em>exo</em>-<em>rig</em> cyclisations to providing a protocol for the radical amination of unactivated alkenes. The α-ester of the amino acid or the urethane groups impart electrophilic behaviour to the aminyl radicals and facilitates cyclisation onto alkenes.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 625-640"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01281-6","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88821420","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Free radical generation by reduction of ketone tosylhydrazones 酮甲酰腙还原生成自由基
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01289-0
Douglass F. Taber, Pramod V. Joshi
{"title":"Free radical generation by reduction of ketone tosylhydrazones","authors":"Douglass F. Taber,&nbsp;Pramod V. Joshi","doi":"10.1016/S1387-1609(01)01289-0","DOIUrl":"10.1016/S1387-1609(01)01289-0","url":null,"abstract":"<div><p>Alkyl radicals are conveniently generated from ketones by reduction of the derived tosylhydrazones. The alkyl radicals undergo efficient intramolecular cyclization to give the thermodynamically less stable <em>cis</em>-1,2-dialkylcyclopentane derivatives.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 557-560"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01289-0","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90662721","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Monoallylstannanes, reagents for allylic radical transfer. Part I 单烯丙基锡烷。烯丙基自由基转移试剂。第一部分
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01287-7
Éric Fouquet , Michel Pereyre , Jean-Claude Rayez , Marie-Thérèse Rayez , Thomas Roulet
{"title":"Monoallylstannanes, reagents for allylic radical transfer. Part I","authors":"Éric Fouquet ,&nbsp;Michel Pereyre ,&nbsp;Jean-Claude Rayez ,&nbsp;Marie-Thérèse Rayez ,&nbsp;Thomas Roulet","doi":"10.1016/S1387-1609(01)01287-7","DOIUrl":"10.1016/S1387-1609(01)01287-7","url":null,"abstract":"<div><p>We have previously highlighted the ability of the <em>N</em>,<em>N</em>-bistrimethylsilylaminostannylene <strong>1</strong> to produce monoallylstannanes <strong>2</strong> in quantitative yields, starting from various functionalised allylic halides via an insertion reaction. In contrast with more electrophilic trihalogenotin radicals, the tin-centred radicals generated from reagents <strong>2</strong> are shown to be the best candidates towards allylic radical transfer, giving allylated products in similar yields as those obtained with classical tributyltin radicals.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 641-648"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01287-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80211558","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Polysusbtituted 1-hydroxycyclopentane carboxylic acid derivatives via a group-selective radical annulation 基团选择性自由基环化的聚双置1-羟基环戊烷羧酸衍生物
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01278-6
Vajira P Bulugahapitiya , Philippe Renaud
{"title":"Polysusbtituted 1-hydroxycyclopentane carboxylic acid derivatives via a group-selective radical annulation","authors":"Vajira P Bulugahapitiya ,&nbsp;Philippe Renaud","doi":"10.1016/S1387-1609(01)01278-6","DOIUrl":"10.1016/S1387-1609(01)01278-6","url":null,"abstract":"<div><p>A radical annulation procedure based on a highly stereoselective conjugated addition of a cyclic 1-hydroxyacid derivative to methyl acrylate followed by a fully group selective cyclization is reported. The 1,3-stereoinduction during the cyclization step is the only component of this process that is not fully controlled. The reaction furnished only two out of the 16 possible diastereomers. This reaction opens a new approach for the preparation of polysubstituted 1-hydroxycyclopentane carboxylic acid derivatives.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 619-624"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01278-6","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76937789","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Détermination de la constante de vitesse de transfert d’hydrogène par le di-n-butyl 4,7,10-trioxaundécylstannane aux radicaux alkyle primaires 测定二正丁基4,7,10-三氧aundecylstannane向伯烷基自由基转移氢的速率常数
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01267-1
Fouad Ferkous , Marie Degueil-Castaing , Hervé Deleuze , Bernard Maillard
{"title":"Détermination de la constante de vitesse de transfert d’hydrogène par le di-n-butyl 4,7,10-trioxaundécylstannane aux radicaux alkyle primaires","authors":"Fouad Ferkous ,&nbsp;Marie Degueil-Castaing ,&nbsp;Hervé Deleuze ,&nbsp;Bernard Maillard","doi":"10.1016/S1387-1609(01)01267-1","DOIUrl":"10.1016/S1387-1609(01)01267-1","url":null,"abstract":"<div><p>The rate constant of hydrogen transfer by dibutyl 4,7,10-trioxaundecylstannane to primary alkyl radicals was determined at different temperatures by the study of the free radical reduction of 6-bromo-1-hexene by this stannane. This work shows that this compound is an excellent substitute to tri-<em>n</em>-butyltinhydride</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 561-565"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01267-1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86219026","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A convenient stereoselective access to new bis-phosphorylated pyrrolidines and their corresponding nitroxides 一种方便的立体选择性获得新的双磷酸化吡咯烷及其相应的氮氧化物
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-07-01 DOI: 10.1016/S1387-1609(01)01282-8
François Le Moigne, Paul Tordo
{"title":"A convenient stereoselective access to new bis-phosphorylated pyrrolidines and their corresponding nitroxides","authors":"François Le Moigne,&nbsp;Paul Tordo","doi":"10.1016/S1387-1609(01)01282-8","DOIUrl":"10.1016/S1387-1609(01)01282-8","url":null,"abstract":"<div><p>Addition of one equivalent of dialkylphosphite to γ-diketones yielded new 5-phosphorylated 1-pyrrolines 3. Depending on the experimental conditions, the addition of a second equivalent of dialkylphosphite to 3, led either to (±)-2,5-bis-phosphorylated pyrrolidines 4 or a mixture of (±)- and <em>meso-</em>4. Pyrrolidines 4 were isolated and subsequently oxidized to the corresponding stable (±)- or <em>meso-</em>nitroxides, 5. Coupling of (±)-5a with the prochiral 2-phenyl-ethyl radical was investigated.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 585-590"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01282-8","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82261122","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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