Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides

Spirocyclic pyrrolidines are structural motifs frequently found in a wide variety of natural products, pharmaceuticals and biologically significant compounds. In the past few years, catalytic asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides have shown to be one of the most straigh...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2018, Vol.16 (15), p.2591-2601
Hauptverfasser: Fang, Xin, Wang, Chun-Jiang
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2601
container_issue 15
container_start_page 2591
container_title Organic & biomolecular chemistry
container_volume 16
creator Fang, Xin
Wang, Chun-Jiang
description Spirocyclic pyrrolidines are structural motifs frequently found in a wide variety of natural products, pharmaceuticals and biologically significant compounds. In the past few years, catalytic asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides have shown to be one of the most straightforward methods for the stereoselective preparation of diverse biologically important spiropyrrolidine heterocycles in high yields with excellent enantioselectivities under mild reaction conditions. In this review, we will discuss the recent major developments in the catalytic enantioselective synthesis of chiral spiropyrrolidine derivatives since 2009.
doi_str_mv 10.1039/C7OB02686B
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2016540485</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2016540485</sourcerecordid><originalsourceid>FETCH-LOGICAL-c381t-5994a88c97cbfe3fa58bf49b8a6cc2cdc5fbd64efb16d2b8fc631e3a65fef54a3</originalsourceid><addsrcrecordid>eNpd0U1LxDAQBuAgiruuXvwBUvAiYjVpPpoc3eIXLOxFzyVNE8zSNjVphfrrjey6gqeZwzMvwwwA5wjeIojFXZGvlzBjnC0PwByRPE8hxeJw32dwBk5C2ECIRM7IMZhlgjIoOJwDW8hBNtNgVSLD1LZ68LFVrguDH9VgXZc4k4TeetdP3rvG1rbTIfm0MkE3OK1t7xrpEzWpxsm6tr8j8svFsPeIkykO6XAKjoxsgj7b1QV4e3x4LZ7T1frppbhfpQpzNKRUCCI5VyJXldHYSMorQ0TFJVMqU7WipqoZ0aZCrM4qbhTDSGPJqNGGEokX4Gqb23v3MeowlK0NSjeN7LQbQ5lBxCiBhNNIL__RjRt9F7eLKssRYRyzqK63SnkXgtem7L1tpZ9KBMufB5R_D4j4Yhc5Vq2u9_T34vgbQbmDAQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2027146836</pqid></control><display><type>article</type><title>Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Fang, Xin ; Wang, Chun-Jiang</creator><creatorcontrib>Fang, Xin ; Wang, Chun-Jiang</creatorcontrib><description>Spirocyclic pyrrolidines are structural motifs frequently found in a wide variety of natural products, pharmaceuticals and biologically significant compounds. In the past few years, catalytic asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides have shown to be one of the most straightforward methods for the stereoselective preparation of diverse biologically important spiropyrrolidine heterocycles in high yields with excellent enantioselectivities under mild reaction conditions. In this review, we will discuss the recent major developments in the catalytic enantioselective synthesis of chiral spiropyrrolidine derivatives since 2009.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/C7OB02686B</identifier><identifier>PMID: 29560980</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Catalysis ; Chemical synthesis ; Cycloaddition ; Enantiomers ; Natural products</subject><ispartof>Organic &amp; biomolecular chemistry, 2018, Vol.16 (15), p.2591-2601</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-5994a88c97cbfe3fa58bf49b8a6cc2cdc5fbd64efb16d2b8fc631e3a65fef54a3</citedby><cites>FETCH-LOGICAL-c381t-5994a88c97cbfe3fa58bf49b8a6cc2cdc5fbd64efb16d2b8fc631e3a65fef54a3</cites><orcidid>0000-0003-3629-6889</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29560980$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fang, Xin</creatorcontrib><creatorcontrib>Wang, Chun-Jiang</creatorcontrib><title>Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Spirocyclic pyrrolidines are structural motifs frequently found in a wide variety of natural products, pharmaceuticals and biologically significant compounds. In the past few years, catalytic asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides have shown to be one of the most straightforward methods for the stereoselective preparation of diverse biologically important spiropyrrolidine heterocycles in high yields with excellent enantioselectivities under mild reaction conditions. In this review, we will discuss the recent major developments in the catalytic enantioselective synthesis of chiral spiropyrrolidine derivatives since 2009.</description><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Cycloaddition</subject><subject>Enantiomers</subject><subject>Natural products</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpd0U1LxDAQBuAgiruuXvwBUvAiYjVpPpoc3eIXLOxFzyVNE8zSNjVphfrrjey6gqeZwzMvwwwA5wjeIojFXZGvlzBjnC0PwByRPE8hxeJw32dwBk5C2ECIRM7IMZhlgjIoOJwDW8hBNtNgVSLD1LZ68LFVrguDH9VgXZc4k4TeetdP3rvG1rbTIfm0MkE3OK1t7xrpEzWpxsm6tr8j8svFsPeIkykO6XAKjoxsgj7b1QV4e3x4LZ7T1frppbhfpQpzNKRUCCI5VyJXldHYSMorQ0TFJVMqU7WipqoZ0aZCrM4qbhTDSGPJqNGGEokX4Gqb23v3MeowlK0NSjeN7LQbQ5lBxCiBhNNIL__RjRt9F7eLKssRYRyzqK63SnkXgtem7L1tpZ9KBMufB5R_D4j4Yhc5Vq2u9_T34vgbQbmDAQ</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Fang, Xin</creator><creator>Wang, Chun-Jiang</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3629-6889</orcidid></search><sort><creationdate>2018</creationdate><title>Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides</title><author>Fang, Xin ; Wang, Chun-Jiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-5994a88c97cbfe3fa58bf49b8a6cc2cdc5fbd64efb16d2b8fc631e3a65fef54a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Cycloaddition</topic><topic>Enantiomers</topic><topic>Natural products</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fang, Xin</creatorcontrib><creatorcontrib>Wang, Chun-Jiang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fang, Xin</au><au>Wang, Chun-Jiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2018</date><risdate>2018</risdate><volume>16</volume><issue>15</issue><spage>2591</spage><epage>2601</epage><pages>2591-2601</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Spirocyclic pyrrolidines are structural motifs frequently found in a wide variety of natural products, pharmaceuticals and biologically significant compounds. In the past few years, catalytic asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides have shown to be one of the most straightforward methods for the stereoselective preparation of diverse biologically important spiropyrrolidine heterocycles in high yields with excellent enantioselectivities under mild reaction conditions. In this review, we will discuss the recent major developments in the catalytic enantioselective synthesis of chiral spiropyrrolidine derivatives since 2009.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>29560980</pmid><doi>10.1039/C7OB02686B</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0003-3629-6889</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof Organic & biomolecular chemistry, 2018, Vol.16 (15), p.2591-2601
issn 1477-0520
1477-0539
language eng
recordid cdi_proquest_miscellaneous_2016540485
source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Catalysis
Chemical synthesis
Cycloaddition
Enantiomers
Natural products
title Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-04T00%3A05%3A59IST&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=Catalytic%20asymmetric%20construction%20of%20spiropyrrolidines%20via%201,3-dipolar%20cycloaddition%20of%20azomethine%20ylides&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Fang,%20Xin&rft.date=2018&rft.volume=16&rft.issue=15&rft.spage=2591&rft.epage=2601&rft.pages=2591-2601&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/C7OB02686B&rft_dat=%3Cproquest_cross%3E2016540485%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=2027146836&rft_id=info:pmid/29560980&rfr_iscdi=true