Enantioselective methodologies using N-carbamoyl-imines

Nucleophilic addition to carbon-nitrogen double bonds (imines) represents one of the most common strategies for the synthesis of amine derivatives. In order to circumvent the problem associated with low reactivity of imines in nucleophilic addition, various imines with electron-withdrawing groups at...

Full description

Saved in:
Bibliographic Details
Published in:Chemical Society reviews 2014-01, Vol.43 (2), p.611-63
Main Authors: Vesely, Jan, Rios, Ramon
Format: Article
Language:English
Subjects:
Amines
Asymmetry
Derivatives
Imines
Nucleophiles
Organic compounds
Strategy
Synthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c470t-beff155490028dd834c098d4d1be0f646206c468864700ac5dadf971a68e27b43
cites cdi_FETCH-LOGICAL-c470t-beff155490028dd834c098d4d1be0f646206c468864700ac5dadf971a68e27b43
container_end_page 63
container_issue 2
container_start_page 611
container_title Chemical Society reviews
container_volume 43
creator Vesely, Jan
Rios, Ramon
description Nucleophilic addition to carbon-nitrogen double bonds (imines) represents one of the most common strategies for the synthesis of amine derivatives. In order to circumvent the problem associated with low reactivity of imines in nucleophilic addition, various imines with electron-withdrawing groups at nitrogen have been studied, and many of them were successfully applied in asymmetric methodologies. Especially N -carbamoyl imines were found to be useful in the enantioselective synthesis of various organic compounds, due to their increased reactivity toward nucleophiles as well as limited difficulties connected with the removal of the carbamoyl moiety in target molecules. The aim of this review is to cover enantioselective methods based on N -carbamoyl imines, focusing on synthetically useful protocols. N -Carbamoyl imines have been shown to be versatile and useful reagents for the synthesis of amino derivatives.
doi_str_mv 10.1039/c3cs60321k
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_C3CS60321K</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1786224568</sourcerecordid><originalsourceid>FETCH-LOGICAL-c470t-beff155490028dd834c098d4d1be0f646206c468864700ac5dadf971a68e27b43</originalsourceid><addsrcrecordid>eNqF0T1PwzAQBmALgWgpLOygsiGkwPkjtjOiqHyICgZgjhzbKYYkLnGC1H9PIKVsMN1J76Mb3kPoEMM5BppcaKoDB0rw2xYaY8YhYoKxbTQGCjwCwGSE9kJ47TcsONlFI8Kw5DRmYyRmtapb54MtrW7dh51Wtn3xxpd-4WyYdsHVi-l9pFWTq8qvyshVrrZhH-0Uqgz2YD0n6Plq9pTeRPOH69v0ch5pJqCNclsUOI5ZAkCkMZIyDYk0zODcQsEZJ8A141LynoPSsVGmSARWXFoickYn6HS4u2z8e2dDm1UuaFuWqra-CxkWkhPCYi7_p0yIOBYEaE_PBqobH0Jji2zZuEo1qwxD9tVpltL08bvTux4fr-92eWXNhv6U2IOjATRBb9Lfp_T5yV95tjQF_QQY74V7</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1477557203</pqid></control><display><type>article</type><title>Enantioselective methodologies using N-carbamoyl-imines</title><source>Royal Society of Chemistry</source><creator>Vesely, Jan ; Rios, Ramon</creator><creatorcontrib>Vesely, Jan ; Rios, Ramon</creatorcontrib><description>Nucleophilic addition to carbon-nitrogen double bonds (imines) represents one of the most common strategies for the synthesis of amine derivatives. In order to circumvent the problem associated with low reactivity of imines in nucleophilic addition, various imines with electron-withdrawing groups at nitrogen have been studied, and many of them were successfully applied in asymmetric methodologies. Especially N -carbamoyl imines were found to be useful in the enantioselective synthesis of various organic compounds, due to their increased reactivity toward nucleophiles as well as limited difficulties connected with the removal of the carbamoyl moiety in target molecules. The aim of this review is to cover enantioselective methods based on N -carbamoyl imines, focusing on synthetically useful protocols. N -Carbamoyl imines have been shown to be versatile and useful reagents for the synthesis of amino derivatives.</description><identifier>ISSN: 0306-0012</identifier><identifier>EISSN: 1460-4744</identifier><identifier>DOI: 10.1039/c3cs60321k</identifier><identifier>PMID: 24186354</identifier><language>eng</language><publisher>England</publisher><subject>Amines ; Asymmetry ; Derivatives ; Imines ; Nucleophiles ; Organic compounds ; Strategy ; Synthesis</subject><ispartof>Chemical Society reviews, 2014-01, Vol.43 (2), p.611-63</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c470t-beff155490028dd834c098d4d1be0f646206c468864700ac5dadf971a68e27b43</citedby><cites>FETCH-LOGICAL-c470t-beff155490028dd834c098d4d1be0f646206c468864700ac5dadf971a68e27b43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24186354$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vesely, Jan</creatorcontrib><creatorcontrib>Rios, Ramon</creatorcontrib><title>Enantioselective methodologies using N-carbamoyl-imines</title><title>Chemical Society reviews</title><addtitle>Chem Soc Rev</addtitle><description>Nucleophilic addition to carbon-nitrogen double bonds (imines) represents one of the most common strategies for the synthesis of amine derivatives. In order to circumvent the problem associated with low reactivity of imines in nucleophilic addition, various imines with electron-withdrawing groups at nitrogen have been studied, and many of them were successfully applied in asymmetric methodologies. Especially N -carbamoyl imines were found to be useful in the enantioselective synthesis of various organic compounds, due to their increased reactivity toward nucleophiles as well as limited difficulties connected with the removal of the carbamoyl moiety in target molecules. The aim of this review is to cover enantioselective methods based on N -carbamoyl imines, focusing on synthetically useful protocols. N -Carbamoyl imines have been shown to be versatile and useful reagents for the synthesis of amino derivatives.</description><subject>Amines</subject><subject>Asymmetry</subject><subject>Derivatives</subject><subject>Imines</subject><subject>Nucleophiles</subject><subject>Organic compounds</subject><subject>Strategy</subject><subject>Synthesis</subject><issn>0306-0012</issn><issn>1460-4744</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqF0T1PwzAQBmALgWgpLOygsiGkwPkjtjOiqHyICgZgjhzbKYYkLnGC1H9PIKVsMN1J76Mb3kPoEMM5BppcaKoDB0rw2xYaY8YhYoKxbTQGCjwCwGSE9kJ47TcsONlFI8Kw5DRmYyRmtapb54MtrW7dh51Wtn3xxpd-4WyYdsHVi-l9pFWTq8qvyshVrrZhH-0Uqgz2YD0n6Plq9pTeRPOH69v0ch5pJqCNclsUOI5ZAkCkMZIyDYk0zODcQsEZJ8A141LynoPSsVGmSARWXFoickYn6HS4u2z8e2dDm1UuaFuWqra-CxkWkhPCYi7_p0yIOBYEaE_PBqobH0Jji2zZuEo1qwxD9tVpltL08bvTux4fr-92eWXNhv6U2IOjATRBb9Lfp_T5yV95tjQF_QQY74V7</recordid><startdate>20140121</startdate><enddate>20140121</enddate><creator>Vesely, Jan</creator><creator>Rios, Ramon</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SP</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20140121</creationdate><title>Enantioselective methodologies using N-carbamoyl-imines</title><author>Vesely, Jan ; Rios, Ramon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c470t-beff155490028dd834c098d4d1be0f646206c468864700ac5dadf971a68e27b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amines</topic><topic>Asymmetry</topic><topic>Derivatives</topic><topic>Imines</topic><topic>Nucleophiles</topic><topic>Organic compounds</topic><topic>Strategy</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vesely, Jan</creatorcontrib><creatorcontrib>Rios, Ramon</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Electronics &amp; Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical Society reviews</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vesely, Jan</au><au>Rios, Ramon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective methodologies using N-carbamoyl-imines</atitle><jtitle>Chemical Society reviews</jtitle><addtitle>Chem Soc Rev</addtitle><date>2014-01-21</date><risdate>2014</risdate><volume>43</volume><issue>2</issue><spage>611</spage><epage>63</epage><pages>611-63</pages><issn>0306-0012</issn><eissn>1460-4744</eissn><abstract>Nucleophilic addition to carbon-nitrogen double bonds (imines) represents one of the most common strategies for the synthesis of amine derivatives. In order to circumvent the problem associated with low reactivity of imines in nucleophilic addition, various imines with electron-withdrawing groups at nitrogen have been studied, and many of them were successfully applied in asymmetric methodologies. Especially N -carbamoyl imines were found to be useful in the enantioselective synthesis of various organic compounds, due to their increased reactivity toward nucleophiles as well as limited difficulties connected with the removal of the carbamoyl moiety in target molecules. The aim of this review is to cover enantioselective methods based on N -carbamoyl imines, focusing on synthetically useful protocols. N -Carbamoyl imines have been shown to be versatile and useful reagents for the synthesis of amino derivatives.</abstract><cop>England</cop><pmid>24186354</pmid><doi>10.1039/c3cs60321k</doi><tpages>2</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0306-0012
ispartof Chemical Society reviews, 2014-01, Vol.43 (2), p.611-63
issn 0306-0012
1460-4744
language eng
recordid cdi_crossref_primary_10_1039_C3CS60321K
source Royal Society of Chemistry
subjects Amines
Asymmetry
Derivatives
Imines
Nucleophiles
Organic compounds
Strategy
Synthesis
title Enantioselective methodologies using N-carbamoyl-imines
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T21%3A52%3A11IST&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=Enantioselective%20methodologies%20using%20N-carbamoyl-imines&rft.jtitle=Chemical%20Society%20reviews&rft.au=Vesely,%20Jan&rft.date=2014-01-21&rft.volume=43&rft.issue=2&rft.spage=611&rft.epage=63&rft.pages=611-63&rft.issn=0306-0012&rft.eissn=1460-4744&rft_id=info:doi/10.1039/c3cs60321k&rft_dat=%3Cproquest_cross%3E1786224568%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c470t-beff155490028dd834c098d4d1be0f646206c468864700ac5dadf971a68e27b43%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1477557203&rft_id=info:pmid/24186354&rfr_iscdi=true