Development of an α’-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein
Aminocatalytic asymmetric conjugate addition of aldehydes to Michael acceptors is a well established C–C bond forming methodology. However, various acrylic-type acceptors, including acrylic acid derivatives and acrolein, remain reluctant. Here we demonstrate that the internal H-bonding self-activati...
| Authors: | ; ; ; ; ; ; |
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| Format: | Article |
| Publication date: | 2023 |
| Country: | España |
| Institution: | Universidad del País Vasco |
| Repository: | Addi. Archivo Digital para la Docencia y la Investigación |
| OAI Identifier: | oai:addi.ehu.eus:10810/64553 |
| Online Access: | http://hdl.handle.net/10810/64553 |
| Access Level: | Open access |
| _version_ | 1878734725500108801 |
|---|---|
| author | Odriozola, José M. |
| author2 | Razkin, Jesús Lorea, Beñat Mielgo Vicente, María Antonia García, Jesús M. Oyarbide Garmendia, Juan Miguel Palomo Nicolau, Claudio |
| author2_role | author author author author author author |
| author_browse | García, Jesús M. Lorea, Beñat Mielgo Vicente, María Antonia Odriozola, José M. Oyarbide Garmendia, Juan Miguel Palomo Nicolau, Claudio Razkin, Jesús |
| author_facet | Odriozola, José M. Razkin, Jesús Lorea, Beñat Mielgo Vicente, María Antonia García, Jesús M. Oyarbide Garmendia, Juan Miguel Palomo Nicolau, Claudio |
| author_role | author |
| collection | Addi. Archivo Digital para la Docencia y la Investigación |
| description | Aminocatalytic asymmetric conjugate addition of aldehydes to Michael acceptors is a well established C–C bond forming methodology. However, various acrylic-type acceptors, including acrylic acid derivatives and acrolein, remain reluctant. Here we demonstrate that the internal H-bonding self-activation in α′-hydroxy enones allows them to react smoothly with enolizable aldehydes using commercially available aminocatalysts to afford adducts in good yields and high enantioselectivity. Straightforward conversion of the ketol moiety of these adducts into aldehyde, ketone and carboxylic acid functionalities offers an indirect, unified entry to products derived from acrolein, alkyl–vinyl ketones and acrylates, respectively. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | ES_6ec8cb20e2a13d4d6b47250c2d8456a1 |
| institution | Universidad del País Vasco |
| instname_str | Universidad del País Vasco |
| network_acronym_str | ES |
| network_name_str | España |
| oai_identifier_str | oai:addi.ehu.eus:10810/64553 |
| publishDate | 2023 |
| publishDateSort | 2023 |
| publisher | Royal Society of Chemistry |
| publisherStr | Royal Society of Chemistry |
| reponame_str | Addi. Archivo Digital para la Docencia y la Investigación |
| spelling | Development of an α’-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein Odriozola, José M. Razkin, Jesús Lorea, Beñat Mielgo Vicente, María Antonia García, Jesús M. Oyarbide Garmendia, Juan Miguel Palomo Nicolau, Claudio Aminocatalytic asymmetric conjugate addition of aldehydes to Michael acceptors is a well established C–C bond forming methodology. However, various acrylic-type acceptors, including acrylic acid derivatives and acrolein, remain reluctant. Here we demonstrate that the internal H-bonding self-activation in α′-hydroxy enones allows them to react smoothly with enolizable aldehydes using commercially available aminocatalysts to afford adducts in good yields and high enantioselectivity. Straightforward conversion of the ketol moiety of these adducts into aldehyde, ketone and carboxylic acid functionalities offers an indirect, unified entry to products derived from acrolein, alkyl–vinyl ketones and acrylates, respectively. Support has been provided by the Basque Government (GV grant IT1583-22), and Ministerio de Ciencia e Innovación (grant PID2019-109633GB/AEI/10.13039/501100011033), Spain.A predoctoral grant to B. L. from Navarra Government (34E/ 2020) is acknowledged Royal Society of Chemistry http://hdl.handle.net/10810/64553 |
| spellingShingle | Development of an α’-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein Odriozola, José M. |
| title | Development of an α’-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein |
| title_full | Development of an α’-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein |
| title_fullStr | Development of an α’-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein |
| title_full_unstemmed | Development of an α’-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein |
| title_short | Development of an α’-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein |
| title_sort | Development of an α’-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein |
| url | http://hdl.handle.net/10810/64553 |