Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative

Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative

A practical asymmetric route to a chiral piperazinone derivative, a fragment of MK-3207, is reported. The amine-bearing benzylic stereocenter is introduced via an asymmetric Pd-catalyzed hydrogenation of a cyclic sulfimidate in the presence of a chiral phosphine ligand. An efficient synthesis of the...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic process research & development 2013-08, Vol.17 (8), p.1052-1060
Hauptverfasser: McLaughlin, Mark, Belyk, Kevin, Chen, Cheng-yi, Linghu, Xin, Pan, Jun, Qian, Gang, Reamer, Robert A, Xu, Yingju
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1060
container_issue 8
container_start_page 1052
container_title Organic process research & development
container_volume 17
creator McLaughlin, Mark
Belyk, Kevin
Chen, Cheng-yi
Linghu, Xin
Pan, Jun
Qian, Gang
Reamer, Robert A
Xu, Yingju
description A practical asymmetric route to a chiral piperazinone derivative, a fragment of MK-3207, is reported. The amine-bearing benzylic stereocenter is introduced via an asymmetric Pd-catalyzed hydrogenation of a cyclic sulfimidate in the presence of a chiral phosphine ligand. An efficient synthesis of the hydrogenation substrate is described, together with process development of the hydrogenation step and elaboration of the resulting cyclic sulfamate product to the desired piperazinone.
doi_str_mv 10.1021/op400150w
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_op400150w</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>a384962080</sourcerecordid><originalsourceid>FETCH-LOGICAL-a325t-67a17120bfaf9f30a8022fe6a5b4b35bcc3da210affcb84f1a23fb62d0fdebf23</originalsourceid><addsrcrecordid>eNptj0tLAzEUhYMoWKsL_8FsXLgYvUkm6bisY31AwYIK7oabTC5N6TxIxsr46x2puHJ1zuLjcD7GzjlccRD8uu0yAK7g84BNuBKQqly_H44dcplqruGYncS4AQCluZiw21VA23uL22Qeh7p2ffA2eRmafu2ij0lLCSbF2ocRWPnOBfzyTdu45M4Fv8Pe79wpOyLcRnf2m1P2dr94LR7T5fPDUzFfpiiF6lM9Qz7jAgwh3ZAEzEEIchqVyYxUxlpZoeCARNbkGXEUkowWFVDlDAk5ZZf7XRvaGIOjsgu-xjCUHMof-fJPfmQv9izaWG7aj9CMz_7hvgEZZloi</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative</title><source>American Chemical Society Journals</source><creator>McLaughlin, Mark ; Belyk, Kevin ; Chen, Cheng-yi ; Linghu, Xin ; Pan, Jun ; Qian, Gang ; Reamer, Robert A ; Xu, Yingju</creator><creatorcontrib>McLaughlin, Mark ; Belyk, Kevin ; Chen, Cheng-yi ; Linghu, Xin ; Pan, Jun ; Qian, Gang ; Reamer, Robert A ; Xu, Yingju</creatorcontrib><description>A practical asymmetric route to a chiral piperazinone derivative, a fragment of MK-3207, is reported. The amine-bearing benzylic stereocenter is introduced via an asymmetric Pd-catalyzed hydrogenation of a cyclic sulfimidate in the presence of a chiral phosphine ligand. An efficient synthesis of the hydrogenation substrate is described, together with process development of the hydrogenation step and elaboration of the resulting cyclic sulfamate product to the desired piperazinone.</description><identifier>ISSN: 1083-6160</identifier><identifier>EISSN: 1520-586X</identifier><identifier>DOI: 10.1021/op400150w</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organic process research &amp; development, 2013-08, Vol.17 (8), p.1052-1060</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a325t-67a17120bfaf9f30a8022fe6a5b4b35bcc3da210affcb84f1a23fb62d0fdebf23</citedby><cites>FETCH-LOGICAL-a325t-67a17120bfaf9f30a8022fe6a5b4b35bcc3da210affcb84f1a23fb62d0fdebf23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/op400150w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/op400150w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>McLaughlin, Mark</creatorcontrib><creatorcontrib>Belyk, Kevin</creatorcontrib><creatorcontrib>Chen, Cheng-yi</creatorcontrib><creatorcontrib>Linghu, Xin</creatorcontrib><creatorcontrib>Pan, Jun</creatorcontrib><creatorcontrib>Qian, Gang</creatorcontrib><creatorcontrib>Reamer, Robert A</creatorcontrib><creatorcontrib>Xu, Yingju</creatorcontrib><title>Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative</title><title>Organic process research &amp; development</title><addtitle>Org. Process Res. Dev</addtitle><description>A practical asymmetric route to a chiral piperazinone derivative, a fragment of MK-3207, is reported. The amine-bearing benzylic stereocenter is introduced via an asymmetric Pd-catalyzed hydrogenation of a cyclic sulfimidate in the presence of a chiral phosphine ligand. An efficient synthesis of the hydrogenation substrate is described, together with process development of the hydrogenation step and elaboration of the resulting cyclic sulfamate product to the desired piperazinone.</description><issn>1083-6160</issn><issn>1520-586X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNptj0tLAzEUhYMoWKsL_8FsXLgYvUkm6bisY31AwYIK7oabTC5N6TxIxsr46x2puHJ1zuLjcD7GzjlccRD8uu0yAK7g84BNuBKQqly_H44dcplqruGYncS4AQCluZiw21VA23uL22Qeh7p2ffA2eRmafu2ij0lLCSbF2ocRWPnOBfzyTdu45M4Fv8Pe79wpOyLcRnf2m1P2dr94LR7T5fPDUzFfpiiF6lM9Qz7jAgwh3ZAEzEEIchqVyYxUxlpZoeCARNbkGXEUkowWFVDlDAk5ZZf7XRvaGIOjsgu-xjCUHMof-fJPfmQv9izaWG7aj9CMz_7hvgEZZloi</recordid><startdate>20130816</startdate><enddate>20130816</enddate><creator>McLaughlin, Mark</creator><creator>Belyk, Kevin</creator><creator>Chen, Cheng-yi</creator><creator>Linghu, Xin</creator><creator>Pan, Jun</creator><creator>Qian, Gang</creator><creator>Reamer, Robert A</creator><creator>Xu, Yingju</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130816</creationdate><title>Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative</title><author>McLaughlin, Mark ; Belyk, Kevin ; Chen, Cheng-yi ; Linghu, Xin ; Pan, Jun ; Qian, Gang ; Reamer, Robert A ; Xu, Yingju</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a325t-67a17120bfaf9f30a8022fe6a5b4b35bcc3da210affcb84f1a23fb62d0fdebf23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McLaughlin, Mark</creatorcontrib><creatorcontrib>Belyk, Kevin</creatorcontrib><creatorcontrib>Chen, Cheng-yi</creatorcontrib><creatorcontrib>Linghu, Xin</creatorcontrib><creatorcontrib>Pan, Jun</creatorcontrib><creatorcontrib>Qian, Gang</creatorcontrib><creatorcontrib>Reamer, Robert A</creatorcontrib><creatorcontrib>Xu, Yingju</creatorcontrib><collection>CrossRef</collection><jtitle>Organic process research &amp; development</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>McLaughlin, Mark</au><au>Belyk, Kevin</au><au>Chen, Cheng-yi</au><au>Linghu, Xin</au><au>Pan, Jun</au><au>Qian, Gang</au><au>Reamer, Robert A</au><au>Xu, Yingju</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative</atitle><jtitle>Organic process research &amp; development</jtitle><addtitle>Org. Process Res. Dev</addtitle><date>2013-08-16</date><risdate>2013</risdate><volume>17</volume><issue>8</issue><spage>1052</spage><epage>1060</epage><pages>1052-1060</pages><issn>1083-6160</issn><eissn>1520-586X</eissn><abstract>A practical asymmetric route to a chiral piperazinone derivative, a fragment of MK-3207, is reported. The amine-bearing benzylic stereocenter is introduced via an asymmetric Pd-catalyzed hydrogenation of a cyclic sulfimidate in the presence of a chiral phosphine ligand. An efficient synthesis of the hydrogenation substrate is described, together with process development of the hydrogenation step and elaboration of the resulting cyclic sulfamate product to the desired piperazinone.</abstract><pub>American Chemical Society</pub><doi>10.1021/op400150w</doi><tpages>9</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1083-6160
ispartof Organic process research & development, 2013-08, Vol.17 (8), p.1052-1060
issn 1083-6160
1520-586X
language eng
recordid cdi_crossref_primary_10_1021_op400150w
source American Chemical Society Journals
title Practical Asymmetric Synthesis of a Chiral Piperazinone Derivative
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-22T10%3A19%3A23IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Practical%20Asymmetric%20Synthesis%20of%20a%20Chiral%20Piperazinone%20Derivative&rft.jtitle=Organic%20process%20research%20&%20development&rft.au=McLaughlin,%20Mark&rft.date=2013-08-16&rft.volume=17&rft.issue=8&rft.spage=1052&rft.epage=1060&rft.pages=1052-1060&rft.issn=1083-6160&rft.eissn=1520-586X&rft_id=info:doi/10.1021/op400150w&rft_dat=%3Cacs_cross%3Ea384962080%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true