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Organo-catalyzed asymmetric cascade annulation reaction for the construction of bi-spirocyclic pyrazolone and oxindole derivatives
A bifunctional organocatalyst catalyzed tandem annulation reaction between β,γ-unsaturated α-ketoesters with α-arylidene pyrazolinones was reported. The tandem Michael–aldol process allows access to optically active bi-spirocyclic pyrazolone and oxindole compounds in high yields with good to excelle...
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Published in: | Organic chemistry frontiers an international journal of organic chemistry 2020-03, Vol.7 (5), p.796-809 |
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container_title | Organic chemistry frontiers an international journal of organic chemistry |
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creator | Bing-Bing Sun Jun-Bo, Chen Jun-Qi, Zhang Xiao-Peng, Yang Hao-Peng, Lv Wang, Zheng Xing-Wang, Wang |
description | A bifunctional organocatalyst catalyzed tandem annulation reaction between β,γ-unsaturated α-ketoesters with α-arylidene pyrazolinones was reported. The tandem Michael–aldol process allows access to optically active bi-spirocyclic pyrazolone and oxindole compounds in high yields with good to excellent enantioselectivity and diastereoselectivity. The resulting bi-spirocyclic compounds possess highly dense functionalized substituents, two all-carbon spiro quaternary stereocenters and one hemiketal stereogenic centers. |
doi_str_mv | 10.1039/d0qo00001a |
format | article |
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The resulting bi-spirocyclic compounds possess highly dense functionalized substituents, two all-carbon spiro quaternary stereocenters and one hemiketal stereogenic centers.</description><subject>Aldehydes</subject><subject>Chemical reactions</subject><subject>Crystallography</subject><subject>Enantiomers</subject><subject>Ketoesters</subject><subject>Optical activity</subject><subject>Organic chemistry</subject><subject>Pyrazolones</subject><subject>Stereoselectivity</subject><issn>2052-4110</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpNkE1LAzEQhoMoWGov_oKA59V87Ef2KMWPQqEXPZdJMqtbtkmbZIvbo7_crfXgXObh5eUZGEJuObvnTNYPlu09G4fDBZkIVogs55xd_uNrMotxc6qIomRFNSHfq_ABzmcGEnTDES2FOGy3mEJrqIFowCIF5_oOUusdDQjmFxofaPpEaryLKfTn0DdUt1nctcGbwXSjYjcEOPrOu5PFUv_VOus7pBZDexiVB4w35KqBLuLsb0_J-_PT2_w1W65eFvPHZWZkJVOmKlTIBdNcWsutsrJRplIV0yAZw1IjL0xhtbSQc6YM6hJrVWrOhclrIeWU3J29u-D3Pca03vg-uPHkWsiyrorxQbn8AV_pZZI</recordid><startdate>20200307</startdate><enddate>20200307</enddate><creator>Bing-Bing Sun</creator><creator>Jun-Bo, Chen</creator><creator>Jun-Qi, Zhang</creator><creator>Xiao-Peng, Yang</creator><creator>Hao-Peng, Lv</creator><creator>Wang, Zheng</creator><creator>Xing-Wang, Wang</creator><general>Royal Society of Chemistry</general><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope></search><sort><creationdate>20200307</creationdate><title>Organo-catalyzed asymmetric cascade annulation reaction for the construction of bi-spirocyclic pyrazolone and oxindole derivatives</title><author>Bing-Bing Sun ; Jun-Bo, Chen ; Jun-Qi, Zhang ; Xiao-Peng, Yang ; Hao-Peng, Lv ; Wang, Zheng ; Xing-Wang, Wang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c373t-87e8e120b13dd1d8d3f8c7870ba300e6be15c5db3da4108ceb6e986b112c49233</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aldehydes</topic><topic>Chemical reactions</topic><topic>Crystallography</topic><topic>Enantiomers</topic><topic>Ketoesters</topic><topic>Optical activity</topic><topic>Organic chemistry</topic><topic>Pyrazolones</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bing-Bing Sun</creatorcontrib><creatorcontrib>Jun-Bo, Chen</creatorcontrib><creatorcontrib>Jun-Qi, Zhang</creatorcontrib><creatorcontrib>Xiao-Peng, Yang</creatorcontrib><creatorcontrib>Hao-Peng, Lv</creatorcontrib><creatorcontrib>Wang, Zheng</creatorcontrib><creatorcontrib>Xing-Wang, Wang</creatorcontrib><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic chemistry frontiers an international journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bing-Bing Sun</au><au>Jun-Bo, Chen</au><au>Jun-Qi, Zhang</au><au>Xiao-Peng, Yang</au><au>Hao-Peng, Lv</au><au>Wang, Zheng</au><au>Xing-Wang, Wang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organo-catalyzed asymmetric cascade annulation reaction for the construction of bi-spirocyclic pyrazolone and oxindole derivatives</atitle><jtitle>Organic chemistry frontiers an international journal of organic chemistry</jtitle><date>2020-03-07</date><risdate>2020</risdate><volume>7</volume><issue>5</issue><spage>796</spage><epage>809</epage><pages>796-809</pages><issn>2052-4110</issn><eissn>2052-4110</eissn><abstract>A bifunctional organocatalyst catalyzed tandem annulation reaction between β,γ-unsaturated α-ketoesters with α-arylidene pyrazolinones was reported. 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subjects | Aldehydes Chemical reactions Crystallography Enantiomers Ketoesters Optical activity Organic chemistry Pyrazolones Stereoselectivity |
title | Organo-catalyzed asymmetric cascade annulation reaction for the construction of bi-spirocyclic pyrazolone and oxindole derivatives |
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