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postgraduate thesis: Studies on the copper hydride mediated reductive aldol addition via enolborates & its applications
Title | Studies on the copper hydride mediated reductive aldol addition via enolborates & its applications |
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Authors | |
Advisors | Advisor(s):Chiu, P |
Issue Date | 2018 |
Publisher | The University of Hong Kong (Pokfulam, Hong Kong) |
Citation | Li, T. [李天樂]. (2018). Studies on the copper hydride mediated reductive aldol addition via enolborates & its applications. (Thesis). University of Hong Kong, Pokfulam, Hong Kong SAR. |
Abstract | A reductive aldol addition via enolborates has been developed. α,β-Unsaturated ketones, esters and amides are used as substrates, reduced by in situ generated copper hydride, from Cu(OAc)2.H2O, phosphine ligand, and with pinacolborane (PinBH) as the stoichiometric reductant. The enolborates thus generated reacted with aromatic, unsaturated, and aliphatic aldehydes to give syn-aldol adducts as the major product with good to excellent yields (up to 98 %) and good syn-diastereoselectivity (up to d.r > 20 : 1). Even for the more challenging substrates such as cyclic, β-monosubstituted or β,β-disubstituted Michael acceptors, synthetically useful aldol products were obtained.
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Degree | Doctor of Philosophy |
Subject | Aldol condensation Reduction (Chemistry) Copper compounds |
Dept/Program | Chemistry |
Persistent Identifier | http://hdl.handle.net/10722/261464 |
DC Field | Value | Language |
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dc.contributor.advisor | Chiu, P | - |
dc.contributor.author | Li, Tin-lok | - |
dc.contributor.author | 李天樂 | - |
dc.date.accessioned | 2018-09-20T06:43:47Z | - |
dc.date.available | 2018-09-20T06:43:47Z | - |
dc.date.issued | 2018 | - |
dc.identifier.citation | Li, T. [李天樂]. (2018). Studies on the copper hydride mediated reductive aldol addition via enolborates & its applications. (Thesis). University of Hong Kong, Pokfulam, Hong Kong SAR. | - |
dc.identifier.uri | http://hdl.handle.net/10722/261464 | - |
dc.description.abstract | A reductive aldol addition via enolborates has been developed. α,β-Unsaturated ketones, esters and amides are used as substrates, reduced by in situ generated copper hydride, from Cu(OAc)2.H2O, phosphine ligand, and with pinacolborane (PinBH) as the stoichiometric reductant. The enolborates thus generated reacted with aromatic, unsaturated, and aliphatic aldehydes to give syn-aldol adducts as the major product with good to excellent yields (up to 98 %) and good syn-diastereoselectivity (up to d.r > 20 : 1). Even for the more challenging substrates such as cyclic, β-monosubstituted or β,β-disubstituted Michael acceptors, synthetically useful aldol products were obtained. | - |
dc.language | eng | - |
dc.publisher | The University of Hong Kong (Pokfulam, Hong Kong) | - |
dc.relation.ispartof | HKU Theses Online (HKUTO) | - |
dc.rights | The author retains all proprietary rights, (such as patent rights) and the right to use in future works. | - |
dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
dc.subject.lcsh | Aldol condensation | - |
dc.subject.lcsh | Reduction (Chemistry) | - |
dc.subject.lcsh | Copper compounds | - |
dc.title | Studies on the copper hydride mediated reductive aldol addition via enolborates & its applications | - |
dc.type | PG_Thesis | - |
dc.description.thesisname | Doctor of Philosophy | - |
dc.description.thesislevel | Doctoral | - |
dc.description.thesisdiscipline | Chemistry | - |
dc.description.nature | published_or_final_version | - |
dc.identifier.doi | 10.5353/th_991044040581703414 | - |
dc.date.hkucongregation | 2018 | - |
dc.identifier.mmsid | 991044040581703414 | - |