A General Method for the α-Acyloxylation of Carbonyl Compounds

A simple, one-pot method for the α-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides th...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2005-12, Vol.7 (25), p.5729-5732
Main Authors: Beshara, Cory S, Hall, Adrian, Jenkins, Robert L, Jones, Kerri L, Jones, Teyrnon C, Killeen, Niall M, Taylor, Paul H, Thomas, Stephen P, Tomkinson, Nicholas C. O
Format: Article
Language:English
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-a313t-eb48b4756da6958456522cbd16c0751d9c703c29a6f8c2747d41979433cc2f663
cites cdi_FETCH-LOGICAL-a313t-eb48b4756da6958456522cbd16c0751d9c703c29a6f8c2747d41979433cc2f663
container_end_page 5732
container_issue 25
container_start_page 5729
container_title Organic letters
container_volume 7
creator Beshara, Cory S
Hall, Adrian
Jenkins, Robert L
Jones, Kerri L
Jones, Teyrnon C
Killeen, Niall M
Taylor, Paul H
Thomas, Stephen P
Tomkinson, Nicholas C. O
description A simple, one-pot method for the α-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the α-functionalized product in 69−92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is regiospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.
doi_str_mv 10.1021/ol052474e
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68857329</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68857329</sourcerecordid><originalsourceid>FETCH-LOGICAL-a313t-eb48b4756da6958456522cbd16c0751d9c703c29a6f8c2747d41979433cc2f663</originalsourceid><addsrcrecordid>eNptkM1KxDAURoMojo4ufAHJRsFFNf9pVzIUHYURN7oOaZIyM6TNmLRgH8sX8ZmszDBuXN17Pw4f3APABUa3GBF8FzzihEnmDsAJ5oRmcrwP97tAE3Ca0hohPCbFMZhgQQlGlJ6A-xmcu9ZF7eGL65bBwjpE2C0d_P7KZmbw4XPwuluFFoYaljpWoR08LEOzCX1r0xk4qrVP7nw3p-D98eGtfMoWr_PncrbINMW0y1zF8opJLqwWBc8ZF5wQU1ksDJIc28JIRA0ptKhzQySTluFCFoxSY0gtBJ2C623vJoaP3qVONatknPe6daFPSuQ5l5QUI3izBU0MKUVXq01cNToOCiP1a0vtbY3s5a60rxpn_8idnhG42gLaJLUOfWzHH_8p-gEVo29T</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68857329</pqid></control><display><type>article</type><title>A General Method for the α-Acyloxylation of Carbonyl Compounds</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Beshara, Cory S ; Hall, Adrian ; Jenkins, Robert L ; Jones, Kerri L ; Jones, Teyrnon C ; Killeen, Niall M ; Taylor, Paul H ; Thomas, Stephen P ; Tomkinson, Nicholas C. O</creator><creatorcontrib>Beshara, Cory S ; Hall, Adrian ; Jenkins, Robert L ; Jones, Kerri L ; Jones, Teyrnon C ; Killeen, Niall M ; Taylor, Paul H ; Thomas, Stephen P ; Tomkinson, Nicholas C. O</creatorcontrib><description>A simple, one-pot method for the α-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the α-functionalized product in 69−92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is regiospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol052474e</identifier><identifier>PMID: 16321033</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2005-12, Vol.7 (25), p.5729-5732</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a313t-eb48b4756da6958456522cbd16c0751d9c703c29a6f8c2747d41979433cc2f663</citedby><cites>FETCH-LOGICAL-a313t-eb48b4756da6958456522cbd16c0751d9c703c29a6f8c2747d41979433cc2f663</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/16321033$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Beshara, Cory S</creatorcontrib><creatorcontrib>Hall, Adrian</creatorcontrib><creatorcontrib>Jenkins, Robert L</creatorcontrib><creatorcontrib>Jones, Kerri L</creatorcontrib><creatorcontrib>Jones, Teyrnon C</creatorcontrib><creatorcontrib>Killeen, Niall M</creatorcontrib><creatorcontrib>Taylor, Paul H</creatorcontrib><creatorcontrib>Thomas, Stephen P</creatorcontrib><creatorcontrib>Tomkinson, Nicholas C. O</creatorcontrib><title>A General Method for the α-Acyloxylation of Carbonyl Compounds</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A simple, one-pot method for the α-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the α-functionalized product in 69−92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is regiospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNptkM1KxDAURoMojo4ufAHJRsFFNf9pVzIUHYURN7oOaZIyM6TNmLRgH8sX8ZmszDBuXN17Pw4f3APABUa3GBF8FzzihEnmDsAJ5oRmcrwP97tAE3Ca0hohPCbFMZhgQQlGlJ6A-xmcu9ZF7eGL65bBwjpE2C0d_P7KZmbw4XPwuluFFoYaljpWoR08LEOzCX1r0xk4qrVP7nw3p-D98eGtfMoWr_PncrbINMW0y1zF8opJLqwWBc8ZF5wQU1ksDJIc28JIRA0ptKhzQySTluFCFoxSY0gtBJ2C623vJoaP3qVONatknPe6daFPSuQ5l5QUI3izBU0MKUVXq01cNToOCiP1a0vtbY3s5a60rxpn_8idnhG42gLaJLUOfWzHH_8p-gEVo29T</recordid><startdate>20051208</startdate><enddate>20051208</enddate><creator>Beshara, Cory S</creator><creator>Hall, Adrian</creator><creator>Jenkins, Robert L</creator><creator>Jones, Kerri L</creator><creator>Jones, Teyrnon C</creator><creator>Killeen, Niall M</creator><creator>Taylor, Paul H</creator><creator>Thomas, Stephen P</creator><creator>Tomkinson, Nicholas C. O</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20051208</creationdate><title>A General Method for the α-Acyloxylation of Carbonyl Compounds</title><author>Beshara, Cory S ; Hall, Adrian ; Jenkins, Robert L ; Jones, Kerri L ; Jones, Teyrnon C ; Killeen, Niall M ; Taylor, Paul H ; Thomas, Stephen P ; Tomkinson, Nicholas C. O</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-eb48b4756da6958456522cbd16c0751d9c703c29a6f8c2747d41979433cc2f663</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Beshara, Cory S</creatorcontrib><creatorcontrib>Hall, Adrian</creatorcontrib><creatorcontrib>Jenkins, Robert L</creatorcontrib><creatorcontrib>Jones, Kerri L</creatorcontrib><creatorcontrib>Jones, Teyrnon C</creatorcontrib><creatorcontrib>Killeen, Niall M</creatorcontrib><creatorcontrib>Taylor, Paul H</creatorcontrib><creatorcontrib>Thomas, Stephen P</creatorcontrib><creatorcontrib>Tomkinson, Nicholas C. O</creatorcontrib><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>Beshara, Cory S</au><au>Hall, Adrian</au><au>Jenkins, Robert L</au><au>Jones, Kerri L</au><au>Jones, Teyrnon C</au><au>Killeen, Niall M</au><au>Taylor, Paul H</au><au>Thomas, Stephen P</au><au>Tomkinson, Nicholas C. O</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A General Method for the α-Acyloxylation of Carbonyl Compounds</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2005-12-08</date><risdate>2005</risdate><volume>7</volume><issue>25</issue><spage>5729</spage><epage>5732</epage><pages>5729-5732</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A simple, one-pot method for the α-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the α-functionalized product in 69−92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is regiospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>16321033</pmid><doi>10.1021/ol052474e</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2005-12, Vol.7 (25), p.5729-5732
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_68857329
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title A General Method for the α-Acyloxylation of Carbonyl Compounds
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T06%3A05%3A42IST&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=A%20General%20Method%20for%20the%20%CE%B1-Acyloxylation%20of%20Carbonyl%20Compounds&rft.jtitle=Organic%20letters&rft.au=Beshara,%20Cory%20S&rft.date=2005-12-08&rft.volume=7&rft.issue=25&rft.spage=5729&rft.epage=5732&rft.pages=5729-5732&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol052474e&rft_dat=%3Cproquest_cross%3E68857329%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a313t-eb48b4756da6958456522cbd16c0751d9c703c29a6f8c2747d41979433cc2f663%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=68857329&rft_id=info:pmid/16321033&rfr_iscdi=true