Cu(I)-Catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases to Ketimines
A copper-catalyzed asymmetric Mannich reaction between glycine Schiff bases and ketimines has been developed. This method afforded 2-oxindole-based chiral syn-α,β-diamino acid derivatives in high yields (89–99%) with good to excellent diastereoselectivities (≤98:2 dr) and excellent enantioselectivit...
Gespeichert in:
Veröffentlicht in: | Journal of organic chemistry 2019-09, Vol.84 (18), p.11639-11648 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 11648 |
---|---|
container_issue | 18 |
container_start_page | 11639 |
container_title | Journal of organic chemistry |
container_volume | 84 |
creator | Fan, Ying Lu, Jian Sha, Feng Li, Qiong Wu, Xin-Yan |
description | A copper-catalyzed asymmetric Mannich reaction between glycine Schiff bases and ketimines has been developed. This method afforded 2-oxindole-based chiral syn-α,β-diamino acid derivatives in high yields (89–99%) with good to excellent diastereoselectivities (≤98:2 dr) and excellent enantioselectivities (95–99% ee). |
doi_str_mv | 10.1021/acs.joc.9b01566 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2281122270</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2281122270</sourcerecordid><originalsourceid>FETCH-LOGICAL-a399t-fc643e904b74aa01ed481f50095262d1185d1c83096a9ee423cdaddaddb6a7bd3</originalsourceid><addsrcrecordid>eNp1kDtPwzAURi0EouUxsyGPRSitH7EbjyWCUlEE4jFbju2orvIocTKEX4-rFDYsSx58vk_3HgCuMJpiRPBMaT_d1noqMoQZ50dgjBlBERcoPgZjhAiJKOF0BM6836JwGGOnYERxHIsYozF4TbvJ6iZKVauK_tsauPB9Wdq2cRo-q6pyegPfrNKtqytY53BZ9NpVFr7rjctzeKe89bCt4ZNtXRk-_AU4yVXh7eXhPQefD_cf6WO0flmu0sU6UlSINso1j6kNY2bzWCmErYkTnDOEBCOcGIwTZrBOKBJcCWtjQrVRZn8zruaZoedgMvTumvqrs76VpfPaFoWqbN15SUiCMSFkjgI6G1Dd1N43Npe7xpWq6SVGcq9RBo0yaJQHjSFxfSjvstKaP_7XWwBuB2BIdk0Vdv237geK7nzF</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2281122270</pqid></control><display><type>article</type><title>Cu(I)-Catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases to Ketimines</title><source>ACS Publications</source><creator>Fan, Ying ; Lu, Jian ; Sha, Feng ; Li, Qiong ; Wu, Xin-Yan</creator><creatorcontrib>Fan, Ying ; Lu, Jian ; Sha, Feng ; Li, Qiong ; Wu, Xin-Yan</creatorcontrib><description>A copper-catalyzed asymmetric Mannich reaction between glycine Schiff bases and ketimines has been developed. This method afforded 2-oxindole-based chiral syn-α,β-diamino acid derivatives in high yields (89–99%) with good to excellent diastereoselectivities (≤98:2 dr) and excellent enantioselectivities (95–99% ee).</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.9b01566</identifier><identifier>PMID: 31449410</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2019-09, Vol.84 (18), p.11639-11648</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a399t-fc643e904b74aa01ed481f50095262d1185d1c83096a9ee423cdaddaddb6a7bd3</citedby><cites>FETCH-LOGICAL-a399t-fc643e904b74aa01ed481f50095262d1185d1c83096a9ee423cdaddaddb6a7bd3</cites><orcidid>0000-0002-6942-7067 ; 0000-0002-0692-1877</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.9b01566$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.9b01566$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,782,786,2767,27083,27931,27932,56745,56795</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31449410$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fan, Ying</creatorcontrib><creatorcontrib>Lu, Jian</creatorcontrib><creatorcontrib>Sha, Feng</creatorcontrib><creatorcontrib>Li, Qiong</creatorcontrib><creatorcontrib>Wu, Xin-Yan</creatorcontrib><title>Cu(I)-Catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases to Ketimines</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A copper-catalyzed asymmetric Mannich reaction between glycine Schiff bases and ketimines has been developed. This method afforded 2-oxindole-based chiral syn-α,β-diamino acid derivatives in high yields (89–99%) with good to excellent diastereoselectivities (≤98:2 dr) and excellent enantioselectivities (95–99% ee).</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kDtPwzAURi0EouUxsyGPRSitH7EbjyWCUlEE4jFbju2orvIocTKEX4-rFDYsSx58vk_3HgCuMJpiRPBMaT_d1noqMoQZ50dgjBlBERcoPgZjhAiJKOF0BM6836JwGGOnYERxHIsYozF4TbvJ6iZKVauK_tsauPB9Wdq2cRo-q6pyegPfrNKtqytY53BZ9NpVFr7rjctzeKe89bCt4ZNtXRk-_AU4yVXh7eXhPQefD_cf6WO0flmu0sU6UlSINso1j6kNY2bzWCmErYkTnDOEBCOcGIwTZrBOKBJcCWtjQrVRZn8zruaZoedgMvTumvqrs76VpfPaFoWqbN15SUiCMSFkjgI6G1Dd1N43Npe7xpWq6SVGcq9RBo0yaJQHjSFxfSjvstKaP_7XWwBuB2BIdk0Vdv237geK7nzF</recordid><startdate>20190920</startdate><enddate>20190920</enddate><creator>Fan, Ying</creator><creator>Lu, Jian</creator><creator>Sha, Feng</creator><creator>Li, Qiong</creator><creator>Wu, Xin-Yan</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6942-7067</orcidid><orcidid>https://orcid.org/0000-0002-0692-1877</orcidid></search><sort><creationdate>20190920</creationdate><title>Cu(I)-Catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases to Ketimines</title><author>Fan, Ying ; Lu, Jian ; Sha, Feng ; Li, Qiong ; Wu, Xin-Yan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a399t-fc643e904b74aa01ed481f50095262d1185d1c83096a9ee423cdaddaddb6a7bd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fan, Ying</creatorcontrib><creatorcontrib>Lu, Jian</creatorcontrib><creatorcontrib>Sha, Feng</creatorcontrib><creatorcontrib>Li, Qiong</creatorcontrib><creatorcontrib>Wu, Xin-Yan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fan, Ying</au><au>Lu, Jian</au><au>Sha, Feng</au><au>Li, Qiong</au><au>Wu, Xin-Yan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cu(I)-Catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases to Ketimines</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2019-09-20</date><risdate>2019</risdate><volume>84</volume><issue>18</issue><spage>11639</spage><epage>11648</epage><pages>11639-11648</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A copper-catalyzed asymmetric Mannich reaction between glycine Schiff bases and ketimines has been developed. This method afforded 2-oxindole-based chiral syn-α,β-diamino acid derivatives in high yields (89–99%) with good to excellent diastereoselectivities (≤98:2 dr) and excellent enantioselectivities (95–99% ee).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31449410</pmid><doi>10.1021/acs.joc.9b01566</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-6942-7067</orcidid><orcidid>https://orcid.org/0000-0002-0692-1877</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0022-3263 |
ispartof | Journal of organic chemistry, 2019-09, Vol.84 (18), p.11639-11648 |
issn | 0022-3263 1520-6904 |
language | eng |
recordid | cdi_proquest_miscellaneous_2281122270 |
source | ACS Publications |
title | Cu(I)-Catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases to Ketimines |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-04T12%3A49%3A30IST&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=Cu(I)-Catalyzed%20Asymmetric%20Mannich%20Reaction%20of%20Glycine%20Schiff%20Bases%20to%20Ketimines&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Fan,%20Ying&rft.date=2019-09-20&rft.volume=84&rft.issue=18&rft.spage=11639&rft.epage=11648&rft.pages=11639-11648&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.9b01566&rft_dat=%3Cproquest_cross%3E2281122270%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=2281122270&rft_id=info:pmid/31449410&rfr_iscdi=true |