Antoine Domain, Guishun Bai, Dr. Juan-Carlos Castillo, Hassane Moussa Abdraman, Prof. Dr. Stéphane Humbel, Dr. Michel Giorgi, Dr. Jean-Valère Naubron, Sara Chentouf, Prof. Dr. Jean Rodriguez, Dr. Xiaoze Bao, Prof. Dr. Damien Bonne
{"title":"Stereocontrol in Conformationally Stable C(sp2)─C(sp3) Atropisomers","authors":"Antoine Domain, Guishun Bai, Dr. Juan-Carlos Castillo, Hassane Moussa Abdraman, Prof. Dr. Stéphane Humbel, Dr. Michel Giorgi, Dr. Jean-Valère Naubron, Sara Chentouf, Prof. Dr. Jean Rodriguez, Dr. Xiaoze Bao, Prof. Dr. Damien Bonne","doi":"10.1002/ange.202506810","DOIUrl":null,"url":null,"abstract":"<p>We report a two-step sequence for the enantioselective construction of a rare family of stable C(sp<sup>2</sup>)─C(sp<sup>3</sup>) atropisomers featuring two additional stereogenic centers. The process begins with an organocatalyzed dihydrobenzofurannulation that establishes and controls the stereochemistry of two carbon centers, followed by a highly diastereoselective functionalization that significantly enhances the barrier to diastereomerization of the C(sp<sup>2</sup>)─C(sp<sup>3</sup>) bond, effectively locking and stabilizing its configuration.</p>","PeriodicalId":7803,"journal":{"name":"Angewandte Chemie","volume":"137 28","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2025-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ange.202506810","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Angewandte Chemie","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/ange.202506810","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
We report a two-step sequence for the enantioselective construction of a rare family of stable C(sp2)─C(sp3) atropisomers featuring two additional stereogenic centers. The process begins with an organocatalyzed dihydrobenzofurannulation that establishes and controls the stereochemistry of two carbon centers, followed by a highly diastereoselective functionalization that significantly enhances the barrier to diastereomerization of the C(sp2)─C(sp3) bond, effectively locking and stabilizing its configuration.