Stereodivergent Synthesis of α,α-Disubstituted α‑Amino Acids via Synergistic Cu/Ir Catalysis

Cu/Ir dual catalysis has been developed for the stereodivergent α-allylation of aldimine esters. The method enables the preparation of a series of nonproteinogenic α-amino acids (α-AAs) bearing two contiguous stereogenic centers in high yield with excellent stereoselectivity. All four product stereo...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2018-01, Vol.140 (4), p.1508-1513
Main Authors: Wei, Liang, Zhu, Qiao, Xu, Shi-Ming, Chang, Xin, Wang, Chun-Jiang
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-a324t-8f0452caaa18e758057e23486b42491202b138df44dc3cc822eb87a449a84e13
cites cdi_FETCH-LOGICAL-a324t-8f0452caaa18e758057e23486b42491202b138df44dc3cc822eb87a449a84e13
container_end_page 1513
container_issue 4
container_start_page 1508
container_title Journal of the American Chemical Society
container_volume 140
creator Wei, Liang
Zhu, Qiao
Xu, Shi-Ming
Chang, Xin
Wang, Chun-Jiang
description Cu/Ir dual catalysis has been developed for the stereodivergent α-allylation of aldimine esters. The method enables the preparation of a series of nonproteinogenic α-amino acids (α-AAs) bearing two contiguous stereogenic centers in high yield with excellent stereoselectivity. All four product stereoisomers could be obtained from the same set of starting materials via pairwise combination of two chiral catalysts. Notably, one-pot protocol could be successfully applied for the preparation of the bimetallic Cu/Ir complexes to simplify the manipulation of Cu/Ir dual catalysis. This method could be further utilized for the construction of the key intermediate of a bioactive pyrrolidine derivative and the concise synthesis of a plant growth regulator (2S,3S)-2-amino-3-cyclopropylbutanoic acid.
doi_str_mv 10.1021/jacs.7b12174
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1989537517</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1989537517</sourcerecordid><originalsourceid>FETCH-LOGICAL-a324t-8f0452caaa18e758057e23486b42491202b138df44dc3cc822eb87a449a84e13</originalsourceid><addsrcrecordid>eNptkLtOwzAUhi0EoqWwMaOMDE3ra-2MVblKlRjaPXIcB1zlUmynUjdegUfpi_QheBIctcDCZB3r-7-j8wNwjeAIQYzGK6nciGcII05PQB8xDGOG8OQU9CGEOOZiQnrgwrlVGCkW6Bz0cEIgYVz0gVx4bXWTm422r7r20WJb-zftjIuaItrvhvtdfGdcmzlvfOt1Hv6-Pj6nlambaKpM7qKNkV0q5E2AVDRrx882mkkvy23wXIKzQpZOXx3fAVg-3C9nT_H85fF5Np3HkmDqY1FAyrCSUiKhOROQcY0JFZOMYpogDHGGiMgLSnNFlBIY60xwSWkiBdWIDMDtQbu2zXurnU8r45QuS1nrpnUpSkTCCGeIB3R4QJVtnLO6SNfWVNJuUwTTrtO06zQ9dhrwm6O5zSqd_8I_Jf6t7lKrprV1uPN_1zfAXIJ4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1989537517</pqid></control><display><type>article</type><title>Stereodivergent Synthesis of α,α-Disubstituted α‑Amino Acids via Synergistic Cu/Ir Catalysis</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Wei, Liang ; Zhu, Qiao ; Xu, Shi-Ming ; Chang, Xin ; Wang, Chun-Jiang</creator><creatorcontrib>Wei, Liang ; Zhu, Qiao ; Xu, Shi-Ming ; Chang, Xin ; Wang, Chun-Jiang</creatorcontrib><description>Cu/Ir dual catalysis has been developed for the stereodivergent α-allylation of aldimine esters. The method enables the preparation of a series of nonproteinogenic α-amino acids (α-AAs) bearing two contiguous stereogenic centers in high yield with excellent stereoselectivity. All four product stereoisomers could be obtained from the same set of starting materials via pairwise combination of two chiral catalysts. Notably, one-pot protocol could be successfully applied for the preparation of the bimetallic Cu/Ir complexes to simplify the manipulation of Cu/Ir dual catalysis. This method could be further utilized for the construction of the key intermediate of a bioactive pyrrolidine derivative and the concise synthesis of a plant growth regulator (2S,3S)-2-amino-3-cyclopropylbutanoic acid.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.7b12174</identifier><identifier>PMID: 29303578</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of the American Chemical Society, 2018-01, Vol.140 (4), p.1508-1513</ispartof><rights>Copyright © 2018 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a324t-8f0452caaa18e758057e23486b42491202b138df44dc3cc822eb87a449a84e13</citedby><cites>FETCH-LOGICAL-a324t-8f0452caaa18e758057e23486b42491202b138df44dc3cc822eb87a449a84e13</cites><orcidid>0000-0003-3629-6889</orcidid></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/29303578$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wei, Liang</creatorcontrib><creatorcontrib>Zhu, Qiao</creatorcontrib><creatorcontrib>Xu, Shi-Ming</creatorcontrib><creatorcontrib>Chang, Xin</creatorcontrib><creatorcontrib>Wang, Chun-Jiang</creatorcontrib><title>Stereodivergent Synthesis of α,α-Disubstituted α‑Amino Acids via Synergistic Cu/Ir Catalysis</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Cu/Ir dual catalysis has been developed for the stereodivergent α-allylation of aldimine esters. The method enables the preparation of a series of nonproteinogenic α-amino acids (α-AAs) bearing two contiguous stereogenic centers in high yield with excellent stereoselectivity. All four product stereoisomers could be obtained from the same set of starting materials via pairwise combination of two chiral catalysts. Notably, one-pot protocol could be successfully applied for the preparation of the bimetallic Cu/Ir complexes to simplify the manipulation of Cu/Ir dual catalysis. This method could be further utilized for the construction of the key intermediate of a bioactive pyrrolidine derivative and the concise synthesis of a plant growth regulator (2S,3S)-2-amino-3-cyclopropylbutanoic acid.</description><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNptkLtOwzAUhi0EoqWwMaOMDE3ra-2MVblKlRjaPXIcB1zlUmynUjdegUfpi_QheBIctcDCZB3r-7-j8wNwjeAIQYzGK6nciGcII05PQB8xDGOG8OQU9CGEOOZiQnrgwrlVGCkW6Bz0cEIgYVz0gVx4bXWTm422r7r20WJb-zftjIuaItrvhvtdfGdcmzlvfOt1Hv6-Pj6nlambaKpM7qKNkV0q5E2AVDRrx882mkkvy23wXIKzQpZOXx3fAVg-3C9nT_H85fF5Np3HkmDqY1FAyrCSUiKhOROQcY0JFZOMYpogDHGGiMgLSnNFlBIY60xwSWkiBdWIDMDtQbu2zXurnU8r45QuS1nrpnUpSkTCCGeIB3R4QJVtnLO6SNfWVNJuUwTTrtO06zQ9dhrwm6O5zSqd_8I_Jf6t7lKrprV1uPN_1zfAXIJ4</recordid><startdate>20180131</startdate><enddate>20180131</enddate><creator>Wei, Liang</creator><creator>Zhu, Qiao</creator><creator>Xu, Shi-Ming</creator><creator>Chang, Xin</creator><creator>Wang, Chun-Jiang</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3629-6889</orcidid></search><sort><creationdate>20180131</creationdate><title>Stereodivergent Synthesis of α,α-Disubstituted α‑Amino Acids via Synergistic Cu/Ir Catalysis</title><author>Wei, Liang ; Zhu, Qiao ; Xu, Shi-Ming ; Chang, Xin ; Wang, Chun-Jiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a324t-8f0452caaa18e758057e23486b42491202b138df44dc3cc822eb87a449a84e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wei, Liang</creatorcontrib><creatorcontrib>Zhu, Qiao</creatorcontrib><creatorcontrib>Xu, Shi-Ming</creatorcontrib><creatorcontrib>Chang, Xin</creatorcontrib><creatorcontrib>Wang, Chun-Jiang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wei, Liang</au><au>Zhu, Qiao</au><au>Xu, Shi-Ming</au><au>Chang, Xin</au><au>Wang, Chun-Jiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereodivergent Synthesis of α,α-Disubstituted α‑Amino Acids via Synergistic Cu/Ir Catalysis</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2018-01-31</date><risdate>2018</risdate><volume>140</volume><issue>4</issue><spage>1508</spage><epage>1513</epage><pages>1508-1513</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Cu/Ir dual catalysis has been developed for the stereodivergent α-allylation of aldimine esters. The method enables the preparation of a series of nonproteinogenic α-amino acids (α-AAs) bearing two contiguous stereogenic centers in high yield with excellent stereoselectivity. All four product stereoisomers could be obtained from the same set of starting materials via pairwise combination of two chiral catalysts. Notably, one-pot protocol could be successfully applied for the preparation of the bimetallic Cu/Ir complexes to simplify the manipulation of Cu/Ir dual catalysis. This method could be further utilized for the construction of the key intermediate of a bioactive pyrrolidine derivative and the concise synthesis of a plant growth regulator (2S,3S)-2-amino-3-cyclopropylbutanoic acid.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>29303578</pmid><doi>10.1021/jacs.7b12174</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-3629-6889</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2018-01, Vol.140 (4), p.1508-1513
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_1989537517
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Stereodivergent Synthesis of α,α-Disubstituted α‑Amino Acids via Synergistic Cu/Ir Catalysis
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T20%3A12%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=Stereodivergent%20Synthesis%20of%20%CE%B1,%CE%B1-Disubstituted%20%CE%B1%E2%80%91Amino%20Acids%20via%20Synergistic%20Cu/Ir%20Catalysis&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Wei,%20Liang&rft.date=2018-01-31&rft.volume=140&rft.issue=4&rft.spage=1508&rft.epage=1513&rft.pages=1508-1513&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/jacs.7b12174&rft_dat=%3Cproquest_cross%3E1989537517%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a324t-8f0452caaa18e758057e23486b42491202b138df44dc3cc822eb87a449a84e13%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1989537517&rft_id=info:pmid/29303578&rfr_iscdi=true