Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis
The cinchona thiourea moiety in the self-assembled modularly designed organocatalysts (MDOs) switches off the iminium catalysis of these catalysts. In this study, it was found that the inhibited iminium catalysis could be switched on by using an appropriate weak acid and that, once the iminium catal...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2021-05, Vol.57 (43), p.5334-5337 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Bora, Pranjal Jakkampudi, Satish Parella, Ramarao Sakkani, Nagaraju Dai, Qipu Bihani, Manisha Arman, Hadi D Zhao, John C.-G |
| description | The cinchona thiourea moiety in the self-assembled modularly designed organocatalysts (MDOs) switches off the iminium catalysis of these catalysts. In this study, it was found that the inhibited iminium catalysis could be switched on by using an appropriate weak acid and that, once the iminium catalysis was switched on, these catalysts could be applied for the highly stereoselective and diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes
via
a domino reaction between ketones and α,β-unsaturated aldehydes.
The inhibited iminium catalysis of the MDOs was switched on by using
trans
-cinnamic acid and the activated MDOs were used for catalyzing the domino Mannich condensation/Michael/Michael reaction between ketones and α,β-unsaturated aldehydes. |
| doi_str_mv | 10.1039/d1cc01020d |
| format | Article |
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via
a domino reaction between ketones and α,β-unsaturated aldehydes.
The inhibited iminium catalysis of the MDOs was switched on by using
trans
-cinnamic acid and the activated MDOs were used for catalyzing the domino Mannich condensation/Michael/Michael reaction between ketones and α,β-unsaturated aldehydes.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d1cc01020d</identifier><identifier>PMID: 33928958</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aldehydes ; Cascade chemical reactions ; Catalysis ; Catalysts ; Crystallography ; Ketones ; Modular design ; Self-assembly ; Stereoselectivity ; Switches</subject><ispartof>Chemical communications (Cambridge, England), 2021-05, Vol.57 (43), p.5334-5337</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-cbb08aad9d658273092310ac6ecf5d2d7991a6775a549301f95aef46716268c73</citedby><cites>FETCH-LOGICAL-c337t-cbb08aad9d658273092310ac6ecf5d2d7991a6775a549301f95aef46716268c73</cites><orcidid>0000-0003-1274-8801 ; 0000-0001-7174-5956</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33928958$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bora, Pranjal</creatorcontrib><creatorcontrib>Jakkampudi, Satish</creatorcontrib><creatorcontrib>Parella, Ramarao</creatorcontrib><creatorcontrib>Sakkani, Nagaraju</creatorcontrib><creatorcontrib>Dai, Qipu</creatorcontrib><creatorcontrib>Bihani, Manisha</creatorcontrib><creatorcontrib>Arman, Hadi D</creatorcontrib><creatorcontrib>Zhao, John C.-G</creatorcontrib><title>Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The cinchona thiourea moiety in the self-assembled modularly designed organocatalysts (MDOs) switches off the iminium catalysis of these catalysts. In this study, it was found that the inhibited iminium catalysis could be switched on by using an appropriate weak acid and that, once the iminium catalysis was switched on, these catalysts could be applied for the highly stereoselective and diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes
via
a domino reaction between ketones and α,β-unsaturated aldehydes.
The inhibited iminium catalysis of the MDOs was switched on by using
trans
-cinnamic acid and the activated MDOs were used for catalyzing the domino Mannich condensation/Michael/Michael reaction between ketones and α,β-unsaturated aldehydes.</description><subject>Aldehydes</subject><subject>Cascade chemical reactions</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Crystallography</subject><subject>Ketones</subject><subject>Modular design</subject><subject>Self-assembly</subject><subject>Stereoselectivity</subject><subject>Switches</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpd0cuKFDEUBuAgijOObtwrATcilOZSuS2l2xsMuFFwV6SSVHeGqqTNqdKpJ_F1TdvtCGaThPOdQ8KP0FNKXlPCzRtPnSOUMOLvoUvKZduIVn-7fzwL0yjeigv0COCG1EWFfoguODdMG6Ev0a9ttDCHErKPP0LZhTRjWNO8DxAB5wG3Tb7NbnVj3odbm4KzpbejD_vVB8D9iheIaYdrA56yX0ZbxhXXUtyl4HEuO5uys7MdV5gBL4ecMPyMs9sfu-qlNsaC4xRTXCZ8lhEeoweDHSE8Oe9X6Ov7d182H5vrzx8-bd5eN45zNTeu74m21hsvhWaKE8M4JdbJ4AbhmVfGUCuVEla0hhM6GGHD0EpFJZPaKX6FXp7mHkr-vgSYuymCC-NYv5oX6JhgRBtihKj0xX_0Ji8l1ddVxVmrqJayqlcn5UoGKGHoDiVOtqwdJd0xrm5LN5s_cW0rfn4eufRT8Hf0bz4VPDuBAu6u-i9v_hsdLp1r</recordid><startdate>20210527</startdate><enddate>20210527</enddate><creator>Bora, Pranjal</creator><creator>Jakkampudi, Satish</creator><creator>Parella, Ramarao</creator><creator>Sakkani, Nagaraju</creator><creator>Dai, Qipu</creator><creator>Bihani, Manisha</creator><creator>Arman, Hadi D</creator><creator>Zhao, John C.-G</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1274-8801</orcidid><orcidid>https://orcid.org/0000-0001-7174-5956</orcidid></search><sort><creationdate>20210527</creationdate><title>Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis</title><author>Bora, Pranjal ; Jakkampudi, Satish ; Parella, Ramarao ; Sakkani, Nagaraju ; Dai, Qipu ; Bihani, Manisha ; Arman, Hadi D ; Zhao, John C.-G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-cbb08aad9d658273092310ac6ecf5d2d7991a6775a549301f95aef46716268c73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aldehydes</topic><topic>Cascade chemical reactions</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Crystallography</topic><topic>Ketones</topic><topic>Modular design</topic><topic>Self-assembly</topic><topic>Stereoselectivity</topic><topic>Switches</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bora, Pranjal</creatorcontrib><creatorcontrib>Jakkampudi, Satish</creatorcontrib><creatorcontrib>Parella, Ramarao</creatorcontrib><creatorcontrib>Sakkani, Nagaraju</creatorcontrib><creatorcontrib>Dai, Qipu</creatorcontrib><creatorcontrib>Bihani, Manisha</creatorcontrib><creatorcontrib>Arman, Hadi D</creatorcontrib><creatorcontrib>Zhao, John C.-G</creatorcontrib><collection>PubMed</collection><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><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bora, Pranjal</au><au>Jakkampudi, Satish</au><au>Parella, Ramarao</au><au>Sakkani, Nagaraju</au><au>Dai, Qipu</au><au>Bihani, Manisha</au><au>Arman, Hadi D</au><au>Zhao, John C.-G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2021-05-27</date><risdate>2021</risdate><volume>57</volume><issue>43</issue><spage>5334</spage><epage>5337</epage><pages>5334-5337</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The cinchona thiourea moiety in the self-assembled modularly designed organocatalysts (MDOs) switches off the iminium catalysis of these catalysts. In this study, it was found that the inhibited iminium catalysis could be switched on by using an appropriate weak acid and that, once the iminium catalysis was switched on, these catalysts could be applied for the highly stereoselective and diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes
via
a domino reaction between ketones and α,β-unsaturated aldehydes.
The inhibited iminium catalysis of the MDOs was switched on by using
trans
-cinnamic acid and the activated MDOs were used for catalyzing the domino Mannich condensation/Michael/Michael reaction between ketones and α,β-unsaturated aldehydes.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>33928958</pmid><doi>10.1039/d1cc01020d</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-1274-8801</orcidid><orcidid>https://orcid.org/0000-0001-7174-5956</orcidid></addata></record> |
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| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2021-05, Vol.57 (43), p.5334-5337 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aldehydes Cascade chemical reactions Catalysis Catalysts Crystallography Ketones Modular design Self-assembly Stereoselectivity Switches |
| title | Diastereodivergent synthesis of 4-oxocyclohexanecarbaldehydes by using the modularly designed organocatalysts upon switching on their iminium catalysis |
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