Catalytic Enantioselective Synthesis of [alpha]-Substituted Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via Vinylaluminum Reagents

One-pot procedure: A general method for the highly enantioselective synthesis of α-substituted allylic alcohols has been developed starting from readily available terminal alkynes and aldehydes and proceeding via vinylaluminum reagents (see scheme, dppp=1,3-bis(diphenylphosphino)propane). The use of...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chemistry : a European journal 2013-12, Vol.19 (52), p.17707-17710
Hauptverfasser:	Kumar, Ravindra, Kawasaki, Hiroki, Harada, Toshiro
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols Aldehydes Alkynes Catalysis Catalysts Chemistry Nickel Synthesis Terminals
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	17710
container_issue	52
container_start_page	17707
container_title	Chemistry : a European journal
container_volume	19
creator	Kumar, Ravindra Kawasaki, Hiroki Harada, Toshiro
description	One-pot procedure: A general method for the highly enantioselective synthesis of α-substituted allylic alcohols has been developed starting from readily available terminal alkynes and aldehydes and proceeding via vinylaluminum reagents (see scheme, dppp=1,3-bis(diphenylphosphino)propane). The use of Me2 AlH is essential in the Ni-catalyzed hydroalumination step to generate vinylaluminum reagents that cannot reduce the aldehyde.
doi_str_mv	10.1002/chem.201303619
format	Article
fullrecord	<record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_miscellaneous_1778009993</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3159678421</sourcerecordid><originalsourceid>FETCH-LOGICAL-g983-e2dde466921aa979c4857ccae7db5545efbe291c266fdaeffeb5fab8e99ae8013</originalsourceid><addsrcrecordid>eNpdkEFr3DAUhEVpINsk15wFvfTijWTZsnVcljQNLASySy4hhGfpOVYqS1tLXvAP6f-tIDn1NG-Gj4E3hFxztuaMlTd6wHFdMi6YkFx9IStel7wQjay_khVTVVPIWqhz8i3Gd8aYkkKsyN8tJHBLspreevDJhogOdbInpPvFpwGjjTT09BnccYCXYj93Mdk0JzR0jzp4A9NCN84tLndsnA5DcJH2UxjpAafRenA5_r14jBS8ybfBYTHZnSzQJ-sXB27O3DzSR4Q39ClekrMeXMSrT70gh5-3h-2vYvdwd7_d7Io31YoCS2OwklKVHEA1Sldt3WgN2Jiurqsa-w5LxXUpZW8A-x67uoeuRaUA2zzUBfnxUXucwp8ZY3odbdToHHgMc3zlTdPmoZQSGf3-H_oe5in_lqlKtkpUrGrEP4a7ews</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1468934047</pqid></control><display><type>article</type><title>Catalytic Enantioselective Synthesis of [alpha]-Substituted Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via Vinylaluminum Reagents</title><source>Wiley Journals</source><creator>Kumar, Ravindra ; Kawasaki, Hiroki ; Harada, Toshiro</creator><creatorcontrib>Kumar, Ravindra ; Kawasaki, Hiroki ; Harada, Toshiro</creatorcontrib><description>One-pot procedure: A general method for the highly enantioselective synthesis of α-substituted allylic alcohols has been developed starting from readily available terminal alkynes and aldehydes and proceeding via vinylaluminum reagents (see scheme, dppp=1,3-bis(diphenylphosphino)propane). The use of Me2 AlH is essential in the Ni-catalyzed hydroalumination step to generate vinylaluminum reagents that cannot reduce the aldehyde.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201303619</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alcohols ; Aldehydes ; Alkynes ; Catalysis ; Catalysts ; Chemistry ; Nickel ; Synthesis ; Terminals</subject><ispartof>Chemistry : a European journal, 2013-12, Vol.19 (52), p.17707-17710</ispartof><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Kumar, Ravindra</creatorcontrib><creatorcontrib>Kawasaki, Hiroki</creatorcontrib><creatorcontrib>Harada, Toshiro</creatorcontrib><title>Catalytic Enantioselective Synthesis of [alpha]-Substituted Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via Vinylaluminum Reagents</title><title>Chemistry : a European journal</title><description>One-pot procedure: A general method for the highly enantioselective synthesis of α-substituted allylic alcohols has been developed starting from readily available terminal alkynes and aldehydes and proceeding via vinylaluminum reagents (see scheme, dppp=1,3-bis(diphenylphosphino)propane). The use of Me2 AlH is essential in the Ni-catalyzed hydroalumination step to generate vinylaluminum reagents that cannot reduce the aldehyde.</description><subject>Alcohols</subject><subject>Aldehydes</subject><subject>Alkynes</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Nickel</subject><subject>Synthesis</subject><subject>Terminals</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNpdkEFr3DAUhEVpINsk15wFvfTijWTZsnVcljQNLASySy4hhGfpOVYqS1tLXvAP6f-tIDn1NG-Gj4E3hFxztuaMlTd6wHFdMi6YkFx9IStel7wQjay_khVTVVPIWqhz8i3Gd8aYkkKsyN8tJHBLspreevDJhogOdbInpPvFpwGjjTT09BnccYCXYj93Mdk0JzR0jzp4A9NCN84tLndsnA5DcJH2UxjpAafRenA5_r14jBS8ybfBYTHZnSzQJ-sXB27O3DzSR4Q39ClekrMeXMSrT70gh5-3h-2vYvdwd7_d7Io31YoCS2OwklKVHEA1Sldt3WgN2Jiurqsa-w5LxXUpZW8A-x67uoeuRaUA2zzUBfnxUXucwp8ZY3odbdToHHgMc3zlTdPmoZQSGf3-H_oe5in_lqlKtkpUrGrEP4a7ews</recordid><startdate>20131223</startdate><enddate>20131223</enddate><creator>Kumar, Ravindra</creator><creator>Kawasaki, Hiroki</creator><creator>Harada, Toshiro</creator><general>Wiley Subscription Services, Inc</general><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope></search><sort><creationdate>20131223</creationdate><title>Catalytic Enantioselective Synthesis of [alpha]-Substituted Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via Vinylaluminum Reagents</title><author>Kumar, Ravindra ; Kawasaki, Hiroki ; Harada, Toshiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g983-e2dde466921aa979c4857ccae7db5545efbe291c266fdaeffeb5fab8e99ae8013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alcohols</topic><topic>Aldehydes</topic><topic>Alkynes</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Nickel</topic><topic>Synthesis</topic><topic>Terminals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumar, Ravindra</creatorcontrib><creatorcontrib>Kawasaki, Hiroki</creatorcontrib><creatorcontrib>Harada, Toshiro</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumar, Ravindra</au><au>Kawasaki, Hiroki</au><au>Harada, Toshiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Enantioselective Synthesis of [alpha]-Substituted Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via Vinylaluminum Reagents</atitle><jtitle>Chemistry : a European journal</jtitle><date>2013-12-23</date><risdate>2013</risdate><volume>19</volume><issue>52</issue><spage>17707</spage><epage>17710</epage><pages>17707-17710</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>One-pot procedure: A general method for the highly enantioselective synthesis of α-substituted allylic alcohols has been developed starting from readily available terminal alkynes and aldehydes and proceeding via vinylaluminum reagents (see scheme, dppp=1,3-bis(diphenylphosphino)propane). The use of Me2 AlH is essential in the Ni-catalyzed hydroalumination step to generate vinylaluminum reagents that cannot reduce the aldehyde.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/chem.201303619</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 0947-6539
ispartof	Chemistry : a European journal, 2013-12, Vol.19 (52), p.17707-17710
issn	0947-6539 1521-3765
language	eng
recordid	cdi_proquest_miscellaneous_1778009993
source	Wiley Journals
subjects	Alcohols Aldehydes Alkynes Catalysis Catalysts Chemistry Nickel Synthesis Terminals
title	Catalytic Enantioselective Synthesis of [alpha]-Substituted Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via Vinylaluminum Reagents
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T10%3A34%3A49IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Catalytic%20Enantioselective%20Synthesis%20of%20%5Balpha%5D-Substituted%20Secondary%20Allylic%20Alcohols%20from%20Terminal%20Alkynes%20and%20Aldehydes%20via%20Vinylaluminum%20Reagents&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Kumar,%20Ravindra&rft.date=2013-12-23&rft.volume=19&rft.issue=52&rft.spage=17707&rft.epage=17710&rft.pages=17707-17710&rft.issn=0947-6539&rft.eissn=1521-3765&rft.coden=CEUJED&rft_id=info:doi/10.1002/chem.201303619&rft_dat=%3Cproquest%3E3159678421%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1468934047&rft_id=info:pmid/&rfr_iscdi=true