Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides

A novel strategy based on phase transfer catalysis for the diastereoselective and enantioselective direct assembly of unsymmetric β,β-diaryl-α-amino acid esters via 1,6-conjugate addition of para-quinone methides and glycine derivatives is described. This protocol also provides an alternative route...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2016-07, Vol.81 (13), p.5655-5662
Main Authors: Zhang, Xiang-Zhi, Deng, Yu-Hua, Yan, Xu, Yu, Ke-Yin, Wang, Fang-Xin, Ma, Xiao-Yan, Fan, Chun-An
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-a333t-8ebd6098c868e59ff7c8c839054aa7ccf3c7b79068f58bb2a1eeac9b194677b63
cites cdi_FETCH-LOGICAL-a333t-8ebd6098c868e59ff7c8c839054aa7ccf3c7b79068f58bb2a1eeac9b194677b63
container_end_page 5662
container_issue 13
container_start_page 5655
container_title Journal of organic chemistry
container_volume 81
creator Zhang, Xiang-Zhi
Deng, Yu-Hua
Yan, Xu
Yu, Ke-Yin
Wang, Fang-Xin
Ma, Xiao-Yan
Fan, Chun-An
description A novel strategy based on phase transfer catalysis for the diastereoselective and enantioselective direct assembly of unsymmetric β,β-diaryl-α-amino acid esters via 1,6-conjugate addition of para-quinone methides and glycine derivatives is described. This protocol also provides an alternative route to the synthetically interesting functionalized chiral tetrahydroisoquinoline and its analogues.
doi_str_mv 10.1021/acs.joc.6b00390
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1801435829</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1801435829</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-8ebd6098c868e59ff7c8c839054aa7ccf3c7b79068f58bb2a1eeac9b194677b63</originalsourceid><addsrcrecordid>eNp1kc1uEzEYRS0EoqGwZoe8RKJO_TP2eJZRKD9SUYWg65HH803raMYOtqdSXog9fZA8E44SEBu8sWWdeyx_F6HXjC4Z5ezS2LTcBLtUHaWioU_QgklOiWpo9RQtKOWcCK7EGXqR0oaWJaV8js54zXnFtVygn--dSRkihAQj2OweABvf4ytvfHb_XH7b-XwPySUcBnzr026aIEdn8f7xYv9IiibuRrL_RVaT8wGvrCuSgznhB2fwTbwzPliTzbjLJcUuFFkHv5nvTAa86ntXXvMH99ZEQ77OReIBf4F873pIL9GzwYwJXp32c3T74er7-hO5vvn4eb26JkYIkYmGrle00VYrDbIZhtqWcxmMrIyprR2Erbu6oUoPUncdNwzA2KZjTaXqulPiHL09ercx_Jgh5XZyycI4Gg9hTi3TlFVCat4U9PKI2hhSijC02-imMoWW0fZQTlvKaUs57amcknhzks_dBP1f_k8bBXh3BI7JOfry1__qfgMKYJ_E</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1801435829</pqid></control><display><type>article</type><title>Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Zhang, Xiang-Zhi ; Deng, Yu-Hua ; Yan, Xu ; Yu, Ke-Yin ; Wang, Fang-Xin ; Ma, Xiao-Yan ; Fan, Chun-An</creator><creatorcontrib>Zhang, Xiang-Zhi ; Deng, Yu-Hua ; Yan, Xu ; Yu, Ke-Yin ; Wang, Fang-Xin ; Ma, Xiao-Yan ; Fan, Chun-An</creatorcontrib><description>A novel strategy based on phase transfer catalysis for the diastereoselective and enantioselective direct assembly of unsymmetric β,β-diaryl-α-amino acid esters via 1,6-conjugate addition of para-quinone methides and glycine derivatives is described. This protocol also provides an alternative route to the synthetically interesting functionalized chiral tetrahydroisoquinoline and its analogues.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.6b00390</identifier><identifier>PMID: 27224285</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2016-07, Vol.81 (13), p.5655-5662</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-8ebd6098c868e59ff7c8c839054aa7ccf3c7b79068f58bb2a1eeac9b194677b63</citedby><cites>FETCH-LOGICAL-a333t-8ebd6098c868e59ff7c8c839054aa7ccf3c7b79068f58bb2a1eeac9b194677b63</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/27224285$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Xiang-Zhi</creatorcontrib><creatorcontrib>Deng, Yu-Hua</creatorcontrib><creatorcontrib>Yan, Xu</creatorcontrib><creatorcontrib>Yu, Ke-Yin</creatorcontrib><creatorcontrib>Wang, Fang-Xin</creatorcontrib><creatorcontrib>Ma, Xiao-Yan</creatorcontrib><creatorcontrib>Fan, Chun-An</creatorcontrib><title>Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A novel strategy based on phase transfer catalysis for the diastereoselective and enantioselective direct assembly of unsymmetric β,β-diaryl-α-amino acid esters via 1,6-conjugate addition of para-quinone methides and glycine derivatives is described. This protocol also provides an alternative route to the synthetically interesting functionalized chiral tetrahydroisoquinoline and its analogues.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp1kc1uEzEYRS0EoqGwZoe8RKJO_TP2eJZRKD9SUYWg65HH803raMYOtqdSXog9fZA8E44SEBu8sWWdeyx_F6HXjC4Z5ezS2LTcBLtUHaWioU_QgklOiWpo9RQtKOWcCK7EGXqR0oaWJaV8js54zXnFtVygn--dSRkihAQj2OweABvf4ytvfHb_XH7b-XwPySUcBnzr026aIEdn8f7xYv9IiibuRrL_RVaT8wGvrCuSgznhB2fwTbwzPliTzbjLJcUuFFkHv5nvTAa86ntXXvMH99ZEQ77OReIBf4F873pIL9GzwYwJXp32c3T74er7-hO5vvn4eb26JkYIkYmGrle00VYrDbIZhtqWcxmMrIyprR2Erbu6oUoPUncdNwzA2KZjTaXqulPiHL09ercx_Jgh5XZyycI4Gg9hTi3TlFVCat4U9PKI2hhSijC02-imMoWW0fZQTlvKaUs57amcknhzks_dBP1f_k8bBXh3BI7JOfry1__qfgMKYJ_E</recordid><startdate>20160701</startdate><enddate>20160701</enddate><creator>Zhang, Xiang-Zhi</creator><creator>Deng, Yu-Hua</creator><creator>Yan, Xu</creator><creator>Yu, Ke-Yin</creator><creator>Wang, Fang-Xin</creator><creator>Ma, Xiao-Yan</creator><creator>Fan, Chun-An</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20160701</creationdate><title>Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides</title><author>Zhang, Xiang-Zhi ; Deng, Yu-Hua ; Yan, Xu ; Yu, Ke-Yin ; Wang, Fang-Xin ; Ma, Xiao-Yan ; Fan, Chun-An</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-8ebd6098c868e59ff7c8c839054aa7ccf3c7b79068f58bb2a1eeac9b194677b63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Xiang-Zhi</creatorcontrib><creatorcontrib>Deng, Yu-Hua</creatorcontrib><creatorcontrib>Yan, Xu</creatorcontrib><creatorcontrib>Yu, Ke-Yin</creatorcontrib><creatorcontrib>Wang, Fang-Xin</creatorcontrib><creatorcontrib>Ma, Xiao-Yan</creatorcontrib><creatorcontrib>Fan, Chun-An</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>Zhang, Xiang-Zhi</au><au>Deng, Yu-Hua</au><au>Yan, Xu</au><au>Yu, Ke-Yin</au><au>Wang, Fang-Xin</au><au>Ma, Xiao-Yan</au><au>Fan, Chun-An</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2016-07-01</date><risdate>2016</risdate><volume>81</volume><issue>13</issue><spage>5655</spage><epage>5662</epage><pages>5655-5662</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A novel strategy based on phase transfer catalysis for the diastereoselective and enantioselective direct assembly of unsymmetric β,β-diaryl-α-amino acid esters via 1,6-conjugate addition of para-quinone methides and glycine derivatives is described. This protocol also provides an alternative route to the synthetically interesting functionalized chiral tetrahydroisoquinoline and its analogues.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>27224285</pmid><doi>10.1021/acs.joc.6b00390</doi><tpages>8</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2016-07, Vol.81 (13), p.5655-5662
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1801435829
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-30T19%3A29%3A48IST&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=Diastereoselective%20and%20Enantioselective%20Synthesis%20of%20Unsymmetric%20%CE%B2,%CE%B2-Diaryl-%CE%B1-Amino%20Acid%20Esters%20via%20Organocatalytic%201,6-Conjugate%20Addition%20of%20para-Quinone%20Methides&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Zhang,%20Xiang-Zhi&rft.date=2016-07-01&rft.volume=81&rft.issue=13&rft.spage=5655&rft.epage=5662&rft.pages=5655-5662&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.6b00390&rft_dat=%3Cproquest_cross%3E1801435829%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a333t-8ebd6098c868e59ff7c8c839054aa7ccf3c7b79068f58bb2a1eeac9b194677b63%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1801435829&rft_id=info:pmid/27224285&rfr_iscdi=true