Asymmetric Mannich Reaction of Imines Derived from Aliphatic and Aromatic Aldehydes Catalyzed by Diarylprolinol Silyl Ether

Anti Mannich, try this! A direct asymmetric Mannich reaction catalyzed by a diarylprolinol silyl ether was developed to afford the anti‐Mannich product with excellent enantioselectivity. Imines derived from both aliphatic and aromatic aldehydes were successfully used to obtain the synthetically impo...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chemistry : a European journal 2011-07, Vol.17 (30), p.8273-8276
Hauptverfasser:	Urushima, Tatsuya, Ishikawa, Hayato, Hayashi, Yujiro
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes Aliphatic compounds asymmetric synthesis Asymmetry Chemical reactions Chemistry domino reactions enantioselectivity Ethers Imines Mannich reaction organocatalysis
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	8276
container_issue	30
container_start_page	8273
container_title	Chemistry : a European journal
container_volume	17
creator	Urushima, Tatsuya Ishikawa, Hayato Hayashi, Yujiro
description	Anti Mannich, try this! A direct asymmetric Mannich reaction catalyzed by a diarylprolinol silyl ether was developed to afford the anti‐Mannich product with excellent enantioselectivity. Imines derived from both aliphatic and aromatic aldehydes were successfully used to obtain the synthetically important β‐amino aldehydes (see scheme; Ts=tosyl). The reaction can also be performed in the presence of water.
doi_str_mv	10.1002/chem.201101077
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_876836456</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3957758901</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5097-d1f2e11711df5664476d3fc1449f4b816ab84f20e360e2026065da929f699913</originalsourceid><addsrcrecordid>eNqF0c9v0zAUB_AIgVgZXDkiSxzGJeW9xHmOj1Xa_ZA6kGDSjpabOKqHkxQ7BQL_PB4dFeIAJ8vW5_tk-5skLxHmCJC9rbemm2eACAhCPEpmWGSY5oKKx8kMJBcpFbk8SZ6FcAcAkvL8aXKSIRVUEp8lPxZh6jozeluza933tt6yD0bXox16NrTsqrO9CWxpvP1iGtb6oWMLZ3dbPcaE7hu2iEe_NgvXmO3URF3pUbvpe_SbiS2t9pPb-cHZfnDso3WTY6txa_zz5EmrXTAvHtbT5OZ8dVNdpuv3F1fVYp3WBUiRNthmBlEgNm1BxLmgJm9r5Fy2fFMi6U3J2wxMTmAyyAioaLTMZEtSSsxPk7PD2HiHz3sTRtXZUBvndG-GfVCloDInXlCUb_4psQTgEgkg0td_0bth7_v4DIWCiBCl4FHND6r2QwjetGrnbRf_QyGo-_7UfX_q2F8MvHoYu990pjny34VFIA_gq3Vm-s84VV2urv8cnh6yNozm2zGr_SdFIheFun13odbL2_M1VFLx_Cc4p7T9</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1766611974</pqid></control><display><type>article</type><title>Asymmetric Mannich Reaction of Imines Derived from Aliphatic and Aromatic Aldehydes Catalyzed by Diarylprolinol Silyl Ether</title><source>Access via Wiley Online Library</source><creator>Urushima, Tatsuya ; Ishikawa, Hayato ; Hayashi, Yujiro</creator><creatorcontrib>Urushima, Tatsuya ; Ishikawa, Hayato ; Hayashi, Yujiro</creatorcontrib><description>Anti Mannich, try this! A direct asymmetric Mannich reaction catalyzed by a diarylprolinol silyl ether was developed to afford the anti‐Mannich product with excellent enantioselectivity. Imines derived from both aliphatic and aromatic aldehydes were successfully used to obtain the synthetically important β‐amino aldehydes (see scheme; Ts=tosyl). The reaction can also be performed in the presence of water.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201101077</identifier><identifier>PMID: 21656864</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aldehydes ; Aliphatic compounds ; asymmetric synthesis ; Asymmetry ; Chemical reactions ; Chemistry ; domino reactions ; enantioselectivity ; Ethers ; Imines ; Mannich reaction ; organocatalysis</subject><ispartof>Chemistry : a European journal, 2011-07, Vol.17 (30), p.8273-8276</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5097-d1f2e11711df5664476d3fc1449f4b816ab84f20e360e2026065da929f699913</citedby><cites>FETCH-LOGICAL-c5097-d1f2e11711df5664476d3fc1449f4b816ab84f20e360e2026065da929f699913</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201101077$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201101077$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21656864$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Urushima, Tatsuya</creatorcontrib><creatorcontrib>Ishikawa, Hayato</creatorcontrib><creatorcontrib>Hayashi, Yujiro</creatorcontrib><title>Asymmetric Mannich Reaction of Imines Derived from Aliphatic and Aromatic Aldehydes Catalyzed by Diarylprolinol Silyl Ether</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Anti Mannich, try this! A direct asymmetric Mannich reaction catalyzed by a diarylprolinol silyl ether was developed to afford the anti‐Mannich product with excellent enantioselectivity. Imines derived from both aliphatic and aromatic aldehydes were successfully used to obtain the synthetically important β‐amino aldehydes (see scheme; Ts=tosyl). The reaction can also be performed in the presence of water.</description><subject>Aldehydes</subject><subject>Aliphatic compounds</subject><subject>asymmetric synthesis</subject><subject>Asymmetry</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>domino reactions</subject><subject>enantioselectivity</subject><subject>Ethers</subject><subject>Imines</subject><subject>Mannich reaction</subject><subject>organocatalysis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqF0c9v0zAUB_AIgVgZXDkiSxzGJeW9xHmOj1Xa_ZA6kGDSjpabOKqHkxQ7BQL_PB4dFeIAJ8vW5_tk-5skLxHmCJC9rbemm2eACAhCPEpmWGSY5oKKx8kMJBcpFbk8SZ6FcAcAkvL8aXKSIRVUEp8lPxZh6jozeluza933tt6yD0bXox16NrTsqrO9CWxpvP1iGtb6oWMLZ3dbPcaE7hu2iEe_NgvXmO3URF3pUbvpe_SbiS2t9pPb-cHZfnDso3WTY6txa_zz5EmrXTAvHtbT5OZ8dVNdpuv3F1fVYp3WBUiRNthmBlEgNm1BxLmgJm9r5Fy2fFMi6U3J2wxMTmAyyAioaLTMZEtSSsxPk7PD2HiHz3sTRtXZUBvndG-GfVCloDInXlCUb_4psQTgEgkg0td_0bth7_v4DIWCiBCl4FHND6r2QwjetGrnbRf_QyGo-_7UfX_q2F8MvHoYu990pjny34VFIA_gq3Vm-s84VV2urv8cnh6yNozm2zGr_SdFIheFun13odbL2_M1VFLx_Cc4p7T9</recordid><startdate>20110718</startdate><enddate>20110718</enddate><creator>Urushima, Tatsuya</creator><creator>Ishikawa, Hayato</creator><creator>Hayashi, Yujiro</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20110718</creationdate><title>Asymmetric Mannich Reaction of Imines Derived from Aliphatic and Aromatic Aldehydes Catalyzed by Diarylprolinol Silyl Ether</title><author>Urushima, Tatsuya ; Ishikawa, Hayato ; Hayashi, Yujiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5097-d1f2e11711df5664476d3fc1449f4b816ab84f20e360e2026065da929f699913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Aldehydes</topic><topic>Aliphatic compounds</topic><topic>asymmetric synthesis</topic><topic>Asymmetry</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>domino reactions</topic><topic>enantioselectivity</topic><topic>Ethers</topic><topic>Imines</topic><topic>Mannich reaction</topic><topic>organocatalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Urushima, Tatsuya</creatorcontrib><creatorcontrib>Ishikawa, Hayato</creatorcontrib><creatorcontrib>Hayashi, Yujiro</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><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><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Urushima, Tatsuya</au><au>Ishikawa, Hayato</au><au>Hayashi, Yujiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Mannich Reaction of Imines Derived from Aliphatic and Aromatic Aldehydes Catalyzed by Diarylprolinol Silyl Ether</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2011-07-18</date><risdate>2011</risdate><volume>17</volume><issue>30</issue><spage>8273</spage><epage>8276</epage><pages>8273-8276</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Anti Mannich, try this! A direct asymmetric Mannich reaction catalyzed by a diarylprolinol silyl ether was developed to afford the anti‐Mannich product with excellent enantioselectivity. Imines derived from both aliphatic and aromatic aldehydes were successfully used to obtain the synthetically important β‐amino aldehydes (see scheme; Ts=tosyl). The reaction can also be performed in the presence of water.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>21656864</pmid><doi>10.1002/chem.201101077</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 0947-6539
ispartof	Chemistry : a European journal, 2011-07, Vol.17 (30), p.8273-8276
issn	0947-6539 1521-3765
language	eng
recordid	cdi_proquest_miscellaneous_876836456
source	Access via Wiley Online Library
subjects	Aldehydes Aliphatic compounds asymmetric synthesis Asymmetry Chemical reactions Chemistry domino reactions enantioselectivity Ethers Imines Mannich reaction organocatalysis
title	Asymmetric Mannich Reaction of Imines Derived from Aliphatic and Aromatic Aldehydes Catalyzed by Diarylprolinol Silyl Ether
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-20T12%3A03%3A34IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Asymmetric%20Mannich%20Reaction%20of%20Imines%20Derived%20from%20Aliphatic%20and%20Aromatic%20Aldehydes%20Catalyzed%20by%20Diarylprolinol%20Silyl%20Ether&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Urushima,%20Tatsuya&rft.date=2011-07-18&rft.volume=17&rft.issue=30&rft.spage=8273&rft.epage=8276&rft.pages=8273-8276&rft.issn=0947-6539&rft.eissn=1521-3765&rft.coden=CEUJED&rft_id=info:doi/10.1002/chem.201101077&rft_dat=%3Cproquest_cross%3E3957758901%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1766611974&rft_id=info:pmid/21656864&rfr_iscdi=true