Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates
Phosphine‐catalyzed enantioselective annulation reactions involving ketimines are a daunting synthetic challenge owing to the intrinsic low reactivity of ketimine substrates. A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin‐derived ketimines as reaction partners was de...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-05, Vol.55 (22), p.6492-6496 |
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| creator | Han, Xiaoyu Chan, Wai-Lun Yao, Weijun Wang, Yongjiang Lu, Yixin |
| description | Phosphine‐catalyzed enantioselective annulation reactions involving ketimines are a daunting synthetic challenge owing to the intrinsic low reactivity of ketimine substrates. A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin‐derived ketimines as reaction partners was developed. Notably, both simple and γ‐substituted allenoates could be utilized, and various 3,2′‐pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98 % ee in all cases).
Like a circle in a spiral: A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin‐derived ketimines as reaction partners has been developed. Both simple and γ‐substituted allenoates could be utilized, and various 3,2′‐pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98 % ee in all cases). |
| doi_str_mv | 10.1002/anie.201600453 |
| format | Article |
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Like a circle in a spiral: A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin‐derived ketimines as reaction partners has been developed. Both simple and γ‐substituted allenoates could be utilized, and various 3,2′‐pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98 % ee in all cases).</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201600453</identifier><identifier>PMID: 27080309</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>[3+2] cycloaddition ; acyclic ketimines ; amino acids ; Chemical reactions ; Cycloaddition ; Enantiomers ; Imines ; Organic chemistry ; Phosphine ; phosphine catalysts ; spirooxindoles ; Substrates</subject><ispartof>Angewandte Chemie International Edition, 2016-05, Vol.55 (22), p.6492-6496</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4763-1e2413fdcfe27c8c91764e7e42d7c5685e9c17bcbb0fe7d1bab0a512d16c8a983</citedby><cites>FETCH-LOGICAL-c4763-1e2413fdcfe27c8c91764e7e42d7c5685e9c17bcbb0fe7d1bab0a512d16c8a983</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201600453$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201600453$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27080309$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Han, Xiaoyu</creatorcontrib><creatorcontrib>Chan, Wai-Lun</creatorcontrib><creatorcontrib>Yao, Weijun</creatorcontrib><creatorcontrib>Wang, Yongjiang</creatorcontrib><creatorcontrib>Lu, Yixin</creatorcontrib><title>Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Phosphine‐catalyzed enantioselective annulation reactions involving ketimines are a daunting synthetic challenge owing to the intrinsic low reactivity of ketimine substrates. A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin‐derived ketimines as reaction partners was developed. Notably, both simple and γ‐substituted allenoates could be utilized, and various 3,2′‐pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98 % ee in all cases).
Like a circle in a spiral: A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin‐derived ketimines as reaction partners has been developed. Both simple and γ‐substituted allenoates could be utilized, and various 3,2′‐pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98 % ee in all cases).</description><subject>[3+2] cycloaddition</subject><subject>acyclic ketimines</subject><subject>amino acids</subject><subject>Chemical reactions</subject><subject>Cycloaddition</subject><subject>Enantiomers</subject><subject>Imines</subject><subject>Organic chemistry</subject><subject>Phosphine</subject><subject>phosphine catalysts</subject><subject>spirooxindoles</subject><subject>Substrates</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkUtv1DAURi0EoqWwZYkisWGTwdd2_FhWZfoQQ2k1INhZjnPDuGSSwU4ow6_H1ZQRYgErX8nnO7r2R8hzoDOglL12fcAZoyApFRV_QA6hYlBypfjDPAvOS6UrOCBPUrrJvNZUPiYHTFFNOTWH5PPVakibVeixXGMT3IhNcR6-rLptMe9dP4YhYYd-DN-xWG5CHPzWd-Gnyxd9cRvGVfEWx7DO-VS4VCynOo0xW9JT8qh1XcJn9-cR-Xg6_3ByXi7en12cHC9KL5TkJSATwNvGt8iU196AkgIVCtYoX0ldofGgal_XtEXVQO1q6ipgDUivndH8iLzaeTdx-DZhGu06JI9d53ocpmRBGSqkyC_O6Mu_0Jthin3ezoKhUjKuafVPSmmjgAluMjXbUT4OKUVs7SaGtYtbC9TeNWPvmrH7ZnLgxb12qvNP7_HfVWTA7IDb0OH2Pzp7fHkx_1Ne7rIhjfhjn3Xxq5WKq8p-ujyzfPnuzeLq-tRe81_w46nO</recordid><startdate>20160523</startdate><enddate>20160523</enddate><creator>Han, Xiaoyu</creator><creator>Chan, Wai-Lun</creator><creator>Yao, Weijun</creator><creator>Wang, Yongjiang</creator><creator>Lu, Yixin</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160523</creationdate><title>Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates</title><author>Han, Xiaoyu ; Chan, Wai-Lun ; Yao, Weijun ; Wang, Yongjiang ; Lu, Yixin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4763-1e2413fdcfe27c8c91764e7e42d7c5685e9c17bcbb0fe7d1bab0a512d16c8a983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>[3+2] cycloaddition</topic><topic>acyclic ketimines</topic><topic>amino acids</topic><topic>Chemical reactions</topic><topic>Cycloaddition</topic><topic>Enantiomers</topic><topic>Imines</topic><topic>Organic chemistry</topic><topic>Phosphine</topic><topic>phosphine catalysts</topic><topic>spirooxindoles</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Han, Xiaoyu</creatorcontrib><creatorcontrib>Chan, Wai-Lun</creatorcontrib><creatorcontrib>Yao, Weijun</creatorcontrib><creatorcontrib>Wang, Yongjiang</creatorcontrib><creatorcontrib>Lu, Yixin</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Han, Xiaoyu</au><au>Chan, Wai-Lun</au><au>Yao, Weijun</au><au>Wang, Yongjiang</au><au>Lu, Yixin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-05-23</date><risdate>2016</risdate><volume>55</volume><issue>22</issue><spage>6492</spage><epage>6496</epage><pages>6492-6496</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Phosphine‐catalyzed enantioselective annulation reactions involving ketimines are a daunting synthetic challenge owing to the intrinsic low reactivity of ketimine substrates. A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin‐derived ketimines as reaction partners was developed. Notably, both simple and γ‐substituted allenoates could be utilized, and various 3,2′‐pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98 % ee in all cases).
Like a circle in a spiral: A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin‐derived ketimines as reaction partners has been developed. Both simple and γ‐substituted allenoates could be utilized, and various 3,2′‐pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98 % ee in all cases).</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27080309</pmid><doi>10.1002/anie.201600453</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | [3+2] cycloaddition acyclic ketimines amino acids Chemical reactions Cycloaddition Enantiomers Imines Organic chemistry Phosphine phosphine catalysts spirooxindoles Substrates |
| title | Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates |
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