Catalytic Asymmetric [2+3] Cyclizations of Azlactones with Azonaphthalenes
The first catalytic asymmetric [2+3] cyclization of azlactones with azonaphthalenes has been established. This strategy allowed the synthesis of a variety of chiral isatin derivatives in generally good yields and excellent enantioselectivities (up to 99 % yield, 98 % ee). The developed reaction has...
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| Veröffentlicht in: | Angewandte Chemie 2018-05, Vol.130 (19), p.5496-5500 |
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| container_title | Angewandte Chemie |
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| creator | Ma, Chun Zhou, Jia‐Yu Zhang, Yi‐Zhu Mei, Guang‐Jian Shi, Feng |
| description | The first catalytic asymmetric [2+3] cyclization of azlactones with azonaphthalenes has been established. This strategy allowed the synthesis of a variety of chiral isatin derivatives in generally good yields and excellent enantioselectivities (up to 99 % yield, 98 % ee). The developed reaction has not only established a catalytic enantioselective [2+3] cyclization using azlactones as two‐carbon building blocks, but also enriches the chemistry of catalytic asymmetric cyclizations of azonaphthalenes. In addition, this protocol will provide a useful method for constructing enantioenriched 3,3′‐disubstituted isatin‐type frameworks.
Dipol‐Ersatz: Die Titelreaktion wurde für Azlactone als C2‐Bausteine und Azonaphthaline als 1,3‐Dipol‐Surrogate entwickelt. Mit dieser Strategie gelang die Synthese vielfältiger chiraler Isatinderivate im Allgemeinen mit guten Ausbeuten und hervorragenden Enantioselektivitäten. CPA=chirale Phosphorsäure. |
| doi_str_mv | 10.1002/ange.201801349 |
| format | Article |
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Dipol‐Ersatz: Die Titelreaktion wurde für Azlactone als C2‐Bausteine und Azonaphthaline als 1,3‐Dipol‐Surrogate entwickelt. Mit dieser Strategie gelang die Synthese vielfältiger chiraler Isatinderivate im Allgemeinen mit guten Ausbeuten und hervorragenden Enantioselektivitäten. CPA=chirale Phosphorsäure.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201801349</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Asymmetrische Katalyse ; Asymmetry ; Azlactone ; Catalysis ; Chemistry ; Cyclisierungen ; Enantiomers ; Enantioselektivität ; Organokatalyse</subject><ispartof>Angewandte Chemie, 2018-05, Vol.130 (19), p.5496-5500</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1629-94b672e4913834d7e9cc6d5196696eda6b2dbdc437257fdeea42fb6703a27d243</citedby><cites>FETCH-LOGICAL-c1629-94b672e4913834d7e9cc6d5196696eda6b2dbdc437257fdeea42fb6703a27d243</cites><orcidid>0000-0003-3922-0708</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.201801349$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201801349$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Ma, Chun</creatorcontrib><creatorcontrib>Zhou, Jia‐Yu</creatorcontrib><creatorcontrib>Zhang, Yi‐Zhu</creatorcontrib><creatorcontrib>Mei, Guang‐Jian</creatorcontrib><creatorcontrib>Shi, Feng</creatorcontrib><title>Catalytic Asymmetric [2+3] Cyclizations of Azlactones with Azonaphthalenes</title><title>Angewandte Chemie</title><description>The first catalytic asymmetric [2+3] cyclization of azlactones with azonaphthalenes has been established. This strategy allowed the synthesis of a variety of chiral isatin derivatives in generally good yields and excellent enantioselectivities (up to 99 % yield, 98 % ee). The developed reaction has not only established a catalytic enantioselective [2+3] cyclization using azlactones as two‐carbon building blocks, but also enriches the chemistry of catalytic asymmetric cyclizations of azonaphthalenes. In addition, this protocol will provide a useful method for constructing enantioenriched 3,3′‐disubstituted isatin‐type frameworks.
Dipol‐Ersatz: Die Titelreaktion wurde für Azlactone als C2‐Bausteine und Azonaphthaline als 1,3‐Dipol‐Surrogate entwickelt. Mit dieser Strategie gelang die Synthese vielfältiger chiraler Isatinderivate im Allgemeinen mit guten Ausbeuten und hervorragenden Enantioselektivitäten. CPA=chirale Phosphorsäure.</description><subject>Asymmetrische Katalyse</subject><subject>Asymmetry</subject><subject>Azlactone</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Cyclisierungen</subject><subject>Enantiomers</subject><subject>Enantioselektivität</subject><subject>Organokatalyse</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkM9LwzAUx4MoOKdXzwWP0vnykibNsZQ5laEXPYmELE1dR9fOJmN0f70dEz16ej_4ft6DDyHXFCYUAO9M8-kmCDQFyrg6ISOaII2ZTOQpGQFwHqfI1Tm58H4FAAKlGpGn3ART96GyUeb79dqFbmjf8ZZ9RHlv62pvQtU2PmrLKNvXxoa2cT7aVWE5zG1jNsuwNLUblpfkrDS1d1c_dUze7qev-UM8f5k95tk8tlSgihVfCImOK8pSxgvplLWiSKgSQglXGLHAYlFYziQmsiycMxzLAQFmUBbI2ZjcHO9uuvZr63zQq3bbNcNLjcAophJADqnJMWW71vvOlXrTVWvT9ZqCPvjSB1_619cAqCOwq2rX_5PW2fNs-sd-Ax6Gbow</recordid><startdate>20180504</startdate><enddate>20180504</enddate><creator>Ma, Chun</creator><creator>Zhou, Jia‐Yu</creator><creator>Zhang, Yi‐Zhu</creator><creator>Mei, Guang‐Jian</creator><creator>Shi, Feng</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-3922-0708</orcidid></search><sort><creationdate>20180504</creationdate><title>Catalytic Asymmetric [2+3] Cyclizations of Azlactones with Azonaphthalenes</title><author>Ma, Chun ; Zhou, Jia‐Yu ; Zhang, Yi‐Zhu ; Mei, Guang‐Jian ; Shi, Feng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1629-94b672e4913834d7e9cc6d5196696eda6b2dbdc437257fdeea42fb6703a27d243</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Asymmetrische Katalyse</topic><topic>Asymmetry</topic><topic>Azlactone</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Cyclisierungen</topic><topic>Enantiomers</topic><topic>Enantioselektivität</topic><topic>Organokatalyse</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ma, Chun</creatorcontrib><creatorcontrib>Zhou, Jia‐Yu</creatorcontrib><creatorcontrib>Zhang, Yi‐Zhu</creatorcontrib><creatorcontrib>Mei, Guang‐Jian</creatorcontrib><creatorcontrib>Shi, Feng</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ma, Chun</au><au>Zhou, Jia‐Yu</au><au>Zhang, Yi‐Zhu</au><au>Mei, Guang‐Jian</au><au>Shi, Feng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Asymmetric [2+3] Cyclizations of Azlactones with Azonaphthalenes</atitle><jtitle>Angewandte Chemie</jtitle><date>2018-05-04</date><risdate>2018</risdate><volume>130</volume><issue>19</issue><spage>5496</spage><epage>5500</epage><pages>5496-5500</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The first catalytic asymmetric [2+3] cyclization of azlactones with azonaphthalenes has been established. This strategy allowed the synthesis of a variety of chiral isatin derivatives in generally good yields and excellent enantioselectivities (up to 99 % yield, 98 % ee). The developed reaction has not only established a catalytic enantioselective [2+3] cyclization using azlactones as two‐carbon building blocks, but also enriches the chemistry of catalytic asymmetric cyclizations of azonaphthalenes. In addition, this protocol will provide a useful method for constructing enantioenriched 3,3′‐disubstituted isatin‐type frameworks.
Dipol‐Ersatz: Die Titelreaktion wurde für Azlactone als C2‐Bausteine und Azonaphthaline als 1,3‐Dipol‐Surrogate entwickelt. Mit dieser Strategie gelang die Synthese vielfältiger chiraler Isatinderivate im Allgemeinen mit guten Ausbeuten und hervorragenden Enantioselektivitäten. CPA=chirale Phosphorsäure.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201801349</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-3922-0708</orcidid></addata></record> |
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| subjects | Asymmetrische Katalyse Asymmetry Azlactone Catalysis Chemistry Cyclisierungen Enantiomers Enantioselektivität Organokatalyse |
| title | Catalytic Asymmetric [2+3] Cyclizations of Azlactones with Azonaphthalenes |
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