Synthesis of sterically hindered ketones from aldehydes via O-silyl oximes

A mild and efficient method to synthesize sterically hindered ketones from aldehydes via O-silyl oximes was developed. Treatment of O-triphenylsilylated oximes with alkyl iodides in the presence of triethyl borane afforded the corresponding ketones.

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2012-07, Vol.53 (27), p.3527-3529
Main Authors: Kim, Joong-Gon, Mishra, Mithilesh Kumar, Jang, Doo Ok
Format: Article
Language:English
Subjects:
Aldehyde
Aldehydes
Boranes
Iodides
Ketone
Ketones
O-triphenylsilylated oxime
Oximes
Synthesis (chemistry)
Tetrahedrons
Triethyl borane
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-c405t-5be48bc8f487cc32073ceb651576f8821d49f06ef63e2a913b56f3d937b0c363
cites cdi_FETCH-LOGICAL-c405t-5be48bc8f487cc32073ceb651576f8821d49f06ef63e2a913b56f3d937b0c363
container_end_page 3529
container_issue 27
container_start_page 3527
container_title Tetrahedron letters
container_volume 53
creator Kim, Joong-Gon
Mishra, Mithilesh Kumar
Jang, Doo Ok
description A mild and efficient method to synthesize sterically hindered ketones from aldehydes via O-silyl oximes was developed. Treatment of O-triphenylsilylated oximes with alkyl iodides in the presence of triethyl borane afforded the corresponding ketones.
doi_str_mv 10.1016/j.tetlet.2012.05.005
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744685876</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040403912007617</els_id><sourcerecordid>1744685876</sourcerecordid><originalsourceid>FETCH-LOGICAL-c405t-5be48bc8f487cc32073ceb651576f8821d49f06ef63e2a913b56f3d937b0c363</originalsourceid><addsrcrecordid>eNp9kEtrwzAQhEVpoenjH_TgYy92V9bD8qVQQp8EcmjuwpZXRKlip5IS6n9fh_TcuSwDMwP7EXJHoaBA5cOmSJg8pqIEWhYgCgBxRmZUVSxnQtFzMgPgkHNg9SW5inEDk6SCGfn4HPu0xuhiNtgsJgzONN6P2dr1HQbssi9MQ48xs2HYZo3vcD12kz24Jlvm0fnRZ8OP22K8IRe28RFv_-41Wb08r-Zv-WL5-j5_WuSGg0i5aJGr1ijLVWUMK6FiBlspqKikVaqkHa8tSLSSYdnUlLVCWtbVrGrBMMmuyf1pdheG7z3GpLcuGvS-6XHYR00rzqUSqjpG-SlqwhBjQKt3wW2bMGoK-khOb_SJnD6S0yD0RG6qPZ5qOH1xcBh0NA57g50LaJLuBvf_wC9P_nlz</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744685876</pqid></control><display><type>article</type><title>Synthesis of sterically hindered ketones from aldehydes via O-silyl oximes</title><source>ScienceDirect Journals</source><creator>Kim, Joong-Gon ; Mishra, Mithilesh Kumar ; Jang, Doo Ok</creator><creatorcontrib>Kim, Joong-Gon ; Mishra, Mithilesh Kumar ; Jang, Doo Ok</creatorcontrib><description>A mild and efficient method to synthesize sterically hindered ketones from aldehydes via O-silyl oximes was developed. Treatment of O-triphenylsilylated oximes with alkyl iodides in the presence of triethyl borane afforded the corresponding ketones.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2012.05.005</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Aldehyde ; Aldehydes ; Boranes ; Iodides ; Ketone ; Ketones ; O-triphenylsilylated oxime ; Oximes ; Synthesis (chemistry) ; Tetrahedrons ; Triethyl borane</subject><ispartof>Tetrahedron letters, 2012-07, Vol.53 (27), p.3527-3529</ispartof><rights>2012 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-5be48bc8f487cc32073ceb651576f8821d49f06ef63e2a913b56f3d937b0c363</citedby><cites>FETCH-LOGICAL-c405t-5be48bc8f487cc32073ceb651576f8821d49f06ef63e2a913b56f3d937b0c363</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></links><search><creatorcontrib>Kim, Joong-Gon</creatorcontrib><creatorcontrib>Mishra, Mithilesh Kumar</creatorcontrib><creatorcontrib>Jang, Doo Ok</creatorcontrib><title>Synthesis of sterically hindered ketones from aldehydes via O-silyl oximes</title><title>Tetrahedron letters</title><description>A mild and efficient method to synthesize sterically hindered ketones from aldehydes via O-silyl oximes was developed. Treatment of O-triphenylsilylated oximes with alkyl iodides in the presence of triethyl borane afforded the corresponding ketones.</description><subject>Aldehyde</subject><subject>Aldehydes</subject><subject>Boranes</subject><subject>Iodides</subject><subject>Ketone</subject><subject>Ketones</subject><subject>O-triphenylsilylated oxime</subject><subject>Oximes</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><subject>Triethyl borane</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9kEtrwzAQhEVpoenjH_TgYy92V9bD8qVQQp8EcmjuwpZXRKlip5IS6n9fh_TcuSwDMwP7EXJHoaBA5cOmSJg8pqIEWhYgCgBxRmZUVSxnQtFzMgPgkHNg9SW5inEDk6SCGfn4HPu0xuhiNtgsJgzONN6P2dr1HQbssi9MQ48xs2HYZo3vcD12kz24Jlvm0fnRZ8OP22K8IRe28RFv_-41Wb08r-Zv-WL5-j5_WuSGg0i5aJGr1ijLVWUMK6FiBlspqKikVaqkHa8tSLSSYdnUlLVCWtbVrGrBMMmuyf1pdheG7z3GpLcuGvS-6XHYR00rzqUSqjpG-SlqwhBjQKt3wW2bMGoK-khOb_SJnD6S0yD0RG6qPZ5qOH1xcBh0NA57g50LaJLuBvf_wC9P_nlz</recordid><startdate>20120704</startdate><enddate>20120704</enddate><creator>Kim, Joong-Gon</creator><creator>Mishra, Mithilesh Kumar</creator><creator>Jang, Doo Ok</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20120704</creationdate><title>Synthesis of sterically hindered ketones from aldehydes via O-silyl oximes</title><author>Kim, Joong-Gon ; Mishra, Mithilesh Kumar ; Jang, Doo Ok</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-5be48bc8f487cc32073ceb651576f8821d49f06ef63e2a913b56f3d937b0c363</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Aldehyde</topic><topic>Aldehydes</topic><topic>Boranes</topic><topic>Iodides</topic><topic>Ketone</topic><topic>Ketones</topic><topic>O-triphenylsilylated oxime</topic><topic>Oximes</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><topic>Triethyl borane</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Joong-Gon</creatorcontrib><creatorcontrib>Mishra, Mithilesh Kumar</creatorcontrib><creatorcontrib>Jang, Doo Ok</creatorcontrib><collection>CrossRef</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>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Joong-Gon</au><au>Mishra, Mithilesh Kumar</au><au>Jang, Doo Ok</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of sterically hindered ketones from aldehydes via O-silyl oximes</atitle><jtitle>Tetrahedron letters</jtitle><date>2012-07-04</date><risdate>2012</risdate><volume>53</volume><issue>27</issue><spage>3527</spage><epage>3529</epage><pages>3527-3529</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>A mild and efficient method to synthesize sterically hindered ketones from aldehydes via O-silyl oximes was developed. Treatment of O-triphenylsilylated oximes with alkyl iodides in the presence of triethyl borane afforded the corresponding ketones.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2012.05.005</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0040-4039
ispartof Tetrahedron letters, 2012-07, Vol.53 (27), p.3527-3529
issn 0040-4039
1873-3581
language eng
recordid cdi_proquest_miscellaneous_1744685876
source ScienceDirect Journals
subjects Aldehyde
Aldehydes
Boranes
Iodides
Ketone
Ketones
O-triphenylsilylated oxime
Oximes
Synthesis (chemistry)
Tetrahedrons
Triethyl borane
title Synthesis of sterically hindered ketones from aldehydes via O-silyl oximes
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T02%3A44%3A58IST&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=Synthesis%20of%20sterically%20hindered%20ketones%20from%20aldehydes%20via%20O-silyl%20oximes&rft.jtitle=Tetrahedron%20letters&rft.au=Kim,%20Joong-Gon&rft.date=2012-07-04&rft.volume=53&rft.issue=27&rft.spage=3527&rft.epage=3529&rft.pages=3527-3529&rft.issn=0040-4039&rft.eissn=1873-3581&rft_id=info:doi/10.1016/j.tetlet.2012.05.005&rft_dat=%3Cproquest_cross%3E1744685876%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c405t-5be48bc8f487cc32073ceb651576f8821d49f06ef63e2a913b56f3d937b0c363%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1744685876&rft_id=info:pmid/&rfr_iscdi=true