Asymmetric Direct Vinylogous Aldol Reaction of Furanone Derivatives Catalyzed by an Axially Chiral Guanidine Base
Ace of Base: The first highly enantioselective direct vinylogous aldol reaction of dihalogenated or α‐thio‐substituted furanones with aldehydes utilizes an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched γ‐substituted butenolides.
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| Veröffentlicht in: | Angewandte Chemie (International ed.) 2010-03, Vol.49 (10), p.1858-1861 |
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| container_end_page | 1861 |
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| container_issue | 10 |
| container_start_page | 1858 |
| container_title | Angewandte Chemie (International ed.) |
| container_volume | 49 |
| creator | Ube, Hitoshi Shimada, Naoki Terada, Masahiro |
| description | Ace of Base: The first highly enantioselective direct vinylogous aldol reaction of dihalogenated or α‐thio‐substituted furanones with aldehydes utilizes an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched γ‐substituted butenolides. |
| doi_str_mv | 10.1002/anie.200906647 |
| format | Article |
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The method provides facile access to enantioenriched γ‐substituted butenolides.</description><subject>aldol reaction</subject><subject>asymmetric catalysis</subject><subject>butenolides</subject><subject>guanidine</subject><subject>organocatalysis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkEFv1DAUhCMEoqVw5Qi-ccpiO4ntHMOmu1SqCoKWHq23zksxOElrJ6Xh1-NVyoobpzeHb0bzJkleM7pilPL30FtccUpLKkQunyTHrOAszaTMnkadZ1kqVcGOkhch_Ii8UlQ8T444ZVkhBDtO7qowdx2O3hpSW49mJN9sP7vhZpgCqVwzOPIFwYx26MnQks3koR96JDV6ew-jvcdA1jCCm39jQ3YzgZ5UDxacm8n6u_XgyHaKLRsbTR8g4MvkWQsu4KvHe5JcbU4v1x_T80_bs3V1npqccpmqHFTDDc0FCNXSFlDsStyprEVZmlxJBhKaAnnRUlM0nLcS4tuNkcCpjPokebfk3vrhbsIw6s4Gg85Bj_E3LbNM5JQqEcnVQho_hOCx1bfeduBnzajer6z3K-vDytHw5jF62nXYHPC_s0agXIBf1uH8nzhdXZyd_hueLl4bRnw4eMH_1EJmstDXF1td11zV15tL_Tnybxe-hUHDjbdBX33dN6FMsbxkNPsD76KizQ</recordid><startdate>20100301</startdate><enddate>20100301</enddate><creator>Ube, Hitoshi</creator><creator>Shimada, Naoki</creator><creator>Terada, Masahiro</creator><general>Wiley-VCH Verlag</general><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>FBQ</scope><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20100301</creationdate><title>Asymmetric Direct Vinylogous Aldol Reaction of Furanone Derivatives Catalyzed by an Axially Chiral Guanidine Base</title><author>Ube, Hitoshi ; Shimada, Naoki ; Terada, Masahiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4027-84a8d2c046a68f0fae6b9eb83fe79c4871a7ad5e25f0c5d22f7a377dc7a2077a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>aldol reaction</topic><topic>asymmetric catalysis</topic><topic>butenolides</topic><topic>guanidine</topic><topic>organocatalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ube, Hitoshi</creatorcontrib><creatorcontrib>Shimada, Naoki</creatorcontrib><creatorcontrib>Terada, Masahiro</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie (International ed.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ube, Hitoshi</au><au>Shimada, Naoki</au><au>Terada, Masahiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Direct Vinylogous Aldol Reaction of Furanone Derivatives Catalyzed by an Axially Chiral Guanidine Base</atitle><jtitle>Angewandte Chemie (International ed.)</jtitle><addtitle>Angewandte Chemie International Edition</addtitle><date>2010-03-01</date><risdate>2010</risdate><volume>49</volume><issue>10</issue><spage>1858</spage><epage>1861</epage><pages>1858-1861</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Ace of Base: The first highly enantioselective direct vinylogous aldol reaction of dihalogenated or α‐thio‐substituted furanones with aldehydes utilizes an axially chiral guanidine base catalyst. 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| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie (International ed.), 2010-03, Vol.49 (10), p.1858-1861 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_733640086 |
| source | Wiley Journals |
| subjects | aldol reaction asymmetric catalysis butenolides guanidine organocatalysis |
| title | Asymmetric Direct Vinylogous Aldol Reaction of Furanone Derivatives Catalyzed by an Axially Chiral Guanidine Base |
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