Chiral Holmium Complex-Catalyzed Diels–Alder Reaction of Silyloxyvinylindoles: Stereoselective Synthesis of Hydrocarbazoles
The catalytic and asymmetric cycloaddition between 3-[1-(silyloxy)vinyl]indoles and electron-deficient olefins gave substituted hydrocarbazoles in up to 99% yield and 94% ee. This reaction was catalyzed by a novel chiral holmium(III) complex. Alkylation of the cycloadduct gave a tricyclic compound w...
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Veröffentlicht in: | Organic letters 2013-10, Vol.15 (20), p.5314-5317 |
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creator | Harada, Shinji Morikawa, Takahiro Nishida, Atsushi |
description | The catalytic and asymmetric cycloaddition between 3-[1-(silyloxy)vinyl]indoles and electron-deficient olefins gave substituted hydrocarbazoles in up to 99% yield and 94% ee. This reaction was catalyzed by a novel chiral holmium(III) complex. Alkylation of the cycloadduct gave a tricyclic compound with four continuous chiral centers, one of which was a quaternary carbon. |
doi_str_mv | 10.1021/ol402559z |
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This reaction was catalyzed by a novel chiral holmium(III) complex. Alkylation of the cycloadduct gave a tricyclic compound with four continuous chiral centers, one of which was a quaternary carbon.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol402559z</identifier><identifier>PMID: 24079531</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkenes - chemistry ; Carbazoles - chemical synthesis ; Carbazoles - chemistry ; Catalysis ; Cyclization ; Holmium - chemistry ; Indoles - chemistry ; Molecular Structure ; Organometallic Compounds - chemistry ; Silanes - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2013-10, Vol.15 (20), p.5314-5317</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-473c67a05691d2cec229e88c6c1a97c0ebab41df2963b506db55ea7f991c6d1b3</citedby><cites>FETCH-LOGICAL-a381t-473c67a05691d2cec229e88c6c1a97c0ebab41df2963b506db55ea7f991c6d1b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol402559z$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol402559z$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24079531$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Harada, Shinji</creatorcontrib><creatorcontrib>Morikawa, Takahiro</creatorcontrib><creatorcontrib>Nishida, Atsushi</creatorcontrib><title>Chiral Holmium Complex-Catalyzed Diels–Alder Reaction of Silyloxyvinylindoles: Stereoselective Synthesis of Hydrocarbazoles</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The catalytic and asymmetric cycloaddition between 3-[1-(silyloxy)vinyl]indoles and electron-deficient olefins gave substituted hydrocarbazoles in up to 99% yield and 94% ee. This reaction was catalyzed by a novel chiral holmium(III) complex. Alkylation of the cycloadduct gave a tricyclic compound with four continuous chiral centers, one of which was a quaternary carbon.</description><subject>Alkenes - chemistry</subject><subject>Carbazoles - chemical synthesis</subject><subject>Carbazoles - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Holmium - chemistry</subject><subject>Indoles - chemistry</subject><subject>Molecular Structure</subject><subject>Organometallic Compounds - chemistry</subject><subject>Silanes - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0N1KwzAUB_Agih_TC19AeiPoRTVJm3bxTurHhIHg9LqkySnLSJuZtLIOBN_BN_RJ7NjclVc5hN_5w_kjdErwFcGUXFsTY8oYX-6gQ8JoFKaY0d3tnOADdOT9DGPS__B9dEBjnHIWkUP0mU21EyYYWVPptgoyW80NLMJMNMJ0S1DBnQbjf76-b40CF7yAkI22dWDLYKJNZ-yi-9B1Z3StrAF_E0wacGA9GOjhBwSTrm6m4LVfrYw65awUrhDLlT5Ge6UwHk427wC9Pdy_ZqNw_Pz4lN2OQxENSRPGaSSTVGCWcKKoBEkph-FQJpIInkoMhShiokrKk6hgOFEFYyDSknMiE0WKaIAu1rlzZ99b8E1eaS_BGFGDbX1O4p7SYZzwnl6uqXTWewdlPne6Eq7LCc5Xbefbtnt7toltiwrUVv7V24PzNRDS5zPburq_8p-gXw6oioA</recordid><startdate>20131018</startdate><enddate>20131018</enddate><creator>Harada, Shinji</creator><creator>Morikawa, Takahiro</creator><creator>Nishida, Atsushi</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20131018</creationdate><title>Chiral Holmium Complex-Catalyzed Diels–Alder Reaction of Silyloxyvinylindoles: Stereoselective Synthesis of Hydrocarbazoles</title><author>Harada, Shinji ; Morikawa, Takahiro ; Nishida, Atsushi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-473c67a05691d2cec229e88c6c1a97c0ebab41df2963b506db55ea7f991c6d1b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkenes - chemistry</topic><topic>Carbazoles - chemical synthesis</topic><topic>Carbazoles - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Holmium - chemistry</topic><topic>Indoles - chemistry</topic><topic>Molecular Structure</topic><topic>Organometallic Compounds - chemistry</topic><topic>Silanes - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Harada, Shinji</creatorcontrib><creatorcontrib>Morikawa, Takahiro</creatorcontrib><creatorcontrib>Nishida, Atsushi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Harada, Shinji</au><au>Morikawa, Takahiro</au><au>Nishida, Atsushi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral Holmium Complex-Catalyzed Diels–Alder Reaction of Silyloxyvinylindoles: Stereoselective Synthesis of Hydrocarbazoles</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2013-10-18</date><risdate>2013</risdate><volume>15</volume><issue>20</issue><spage>5314</spage><epage>5317</epage><pages>5314-5317</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The catalytic and asymmetric cycloaddition between 3-[1-(silyloxy)vinyl]indoles and electron-deficient olefins gave substituted hydrocarbazoles in up to 99% yield and 94% ee. This reaction was catalyzed by a novel chiral holmium(III) complex. Alkylation of the cycloadduct gave a tricyclic compound with four continuous chiral centers, one of which was a quaternary carbon.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24079531</pmid><doi>10.1021/ol402559z</doi><tpages>4</tpages></addata></record> |
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subjects | Alkenes - chemistry Carbazoles - chemical synthesis Carbazoles - chemistry Catalysis Cyclization Holmium - chemistry Indoles - chemistry Molecular Structure Organometallic Compounds - chemistry Silanes - chemistry Stereoisomerism |
title | Chiral Holmium Complex-Catalyzed Diels–Alder Reaction of Silyloxyvinylindoles: Stereoselective Synthesis of Hydrocarbazoles |
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