Jyotish Barman, Spoorthi Ananda, Subhas Chandra Pan
{"title":"Stereoselective (3 + 3)-Cycloannulation of Carbonyl Ylides and (<i>Z</i>)-3-Benzylidene-3<i>H</i>-indoles Enabled by Cooperative Rh/Chiral Phosphoric Acid Catalysis.","authors":"Jyotish Barman, Spoorthi Ananda, Subhas Chandra Pan","doi":"10.1021/acs.orglett.5c00188","DOIUrl":null,"url":null,"abstract":"<p><p>A diastereo- and enantioselective (3 + 3)-cycloannulation of in situ generated carbonyl ylides and (<i>Z</i>)-3-benzylidene-3<i>H</i>-indoles enabled by cooperative Rh/chiral phosphoric acid catalysis is reported. This study is the first to describe an enantioselective synthesis of cyclohepta[<i>b</i>]indole with an oxa-bridged motif. The scope of the reaction is broad, and the oxa-bridged cyclohepta[<i>b</i>]indole products were obtained in moderate to good yields and with excellent diastereoselectivities and good to high enantioselectivities.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00188","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A diastereo- and enantioselective (3 + 3)-cycloannulation of in situ generated carbonyl ylides and (Z)-3-benzylidene-3H-indoles enabled by cooperative Rh/chiral phosphoric acid catalysis is reported. This study is the first to describe an enantioselective synthesis of cyclohepta[b]indole with an oxa-bridged motif. The scope of the reaction is broad, and the oxa-bridged cyclohepta[b]indole products were obtained in moderate to good yields and with excellent diastereoselectivities and good to high enantioselectivities.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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