Synthesis of amino alcohols through one-popt catalytic boron addition sequences
Amino alcohols are important building blocks extensively employed for the synthesis of natural products, pharmaceuticals, and for the production of chiral auxiliaries or catalysts used in asymmetric synthesis. Organoboranes can be utilized as interesting intermediates in organic chemistry. Taking in...
| Author: | |
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| Format: | Doctoral thesis |
| Status: | Published version |
| Publication date: | 2013 |
| Country: | España |
| Institution: | Universitat Rovira i virgili (URV) |
| Repository: | Repositori Institucional de la Universitat Rovira i Virgili |
| OAI Identifier: | oai:urv.cat:TDX:1255 |
| Online Access: | https://hdl.handle.net/20.500.11797/TDX1255 http://hdl.handle.net/10803/126444 |
| Access Level: | Open access |
| Keyword: | 547 - Química orgànica 546 - Química inorgànica 54 - Química |
| _version_ | 1878733902429814785 |
|---|---|
| author | Solé Marcé, Cristina |
| author_browse | Solé Marcé, Cristina |
| author_facet | Solé Marcé, Cristina |
| author_role | author |
| collection | Repositori Institucional de la Universitat Rovira i Virgili |
| description | Amino alcohols are important building blocks extensively employed for the synthesis of natural products, pharmaceuticals, and for the production of chiral auxiliaries or catalysts used in asymmetric synthesis. Organoboranes can be utilized as interesting intermediates in organic chemistry. Taking into consideration the advantages of organoboronic esters and the importance of amino alcohols, four new one-pot routes to synthesize β– or γ–amino alcohols have been developed in this thesis. The first and the second were based on the catalytic β–boration of α,β–unsaturated imines followed by reduction of the corresponding imines and oxidation of C-B bond to obtain the desired γ–amino alcohol structure. The third was based on the organocatalytic β–amination of α,β–unsaturated ketones followed by the reduction of the C=O double bond. The last route was developed to synthesize β–amino alcohol, based on the enantioselective organocatalytic boryl addition to tosylaldimines followed by homologation/oxidation sequence. |
| eu_rights_str_mv | openAccess |
| format | doctoralThesis |
| id | ES_5f3db9aeecbf2b4fbb606b2bcc3facac |
| institution | Universitat Rovira i virgili (URV) |
| instname_str | Universitat Rovira i virgili (URV) |
| network_acronym_str | ES |
| network_name_str | España |
| oai_identifier_str | oai:urv.cat:TDX:1255 |
| publishDate | 2013 |
| publishDateSort | 2013 |
| publisher | Universitat Rovira i Virgili |
| publisherStr | Universitat Rovira i Virgili |
| reponame_str | Repositori Institucional de la Universitat Rovira i Virgili |
| spelling | Synthesis of amino alcohols through one-popt catalytic boron addition sequences Solé Marcé, Cristina 547 - Química orgànica 546 - Química inorgànica 54 - Química Amino alcohols are important building blocks extensively employed for the synthesis of natural products, pharmaceuticals, and for the production of chiral auxiliaries or catalysts used in asymmetric synthesis. Organoboranes can be utilized as interesting intermediates in organic chemistry. Taking into consideration the advantages of organoboronic esters and the importance of amino alcohols, four new one-pot routes to synthesize β– or γ–amino alcohols have been developed in this thesis. The first and the second were based on the catalytic β–boration of α,β–unsaturated imines followed by reduction of the corresponding imines and oxidation of C-B bond to obtain the desired γ–amino alcohol structure. The third was based on the organocatalytic β–amination of α,β–unsaturated ketones followed by the reduction of the C=O double bond. The last route was developed to synthesize β–amino alcohol, based on the enantioselective organocatalytic boryl addition to tosylaldimines followed by homologation/oxidation sequence. Els amino alcohols són estructures importants usades en la síntesis de productes naturals, fàrmacs i auxiliars o catalitzadors quirals aplicats en la síntesis orgànica asimètrica. Els organoborans poden ser utilitzats com intermedis versàtils en la síntesis orgànica. Tenint en compte l’ús dels organoborans i la importància dels amino alcohols, quatre noves rutes “one-pot” han estat desenvolupades en aquesta tesis per sintetitzar β– o γ–amino alcohols. Les dos primeres rutes estan basades en la β–boració catalítica d’imines α,β–insaturades seguida per la reducció de la imina corresponent i l’oxidació de l’enllaç C-B per obtenir l’estructura γ–amino alcohol desitjada. La tercera ruta consistia en una β-aminació organocatalítica de cetones α,β–insaturades seguida per la reducció del doble enllaç C=O in situ. L’última ruta va ser dissenyada per la síntesis dels β–amino alcohols, basada en l’addició organocatalítica del bor a tosilaldimines seguida pel procés d’homologació/oxidació. Universitat Rovira i Virgili https://hdl.handle.net/20.500.11797/TDX1255 http://hdl.handle.net/10803/126444 |
| spellingShingle | Synthesis of amino alcohols through one-popt catalytic boron addition sequences Solé Marcé, Cristina 547 - Química orgànica 546 - Química inorgànica 54 - Química |
| status_str | publishedVersion |
| title | Synthesis of amino alcohols through one-popt catalytic boron addition sequences |
| title_full | Synthesis of amino alcohols through one-popt catalytic boron addition sequences |
| title_fullStr | Synthesis of amino alcohols through one-popt catalytic boron addition sequences |
| title_full_unstemmed | Synthesis of amino alcohols through one-popt catalytic boron addition sequences |
| title_short | Synthesis of amino alcohols through one-popt catalytic boron addition sequences |
| title_sort | Synthesis of amino alcohols through one-popt catalytic boron addition sequences |
| topic | 547 - Química orgànica 546 - Química inorgànica 54 - Química |
| topic_facet | 547 - Química orgànica 546 - Química inorgànica 54 - Química |
| url | https://hdl.handle.net/20.500.11797/TDX1255 http://hdl.handle.net/10803/126444 |