Unraveling the Role of Supramolecular Additives in a Proline‐Catalyzed Reaction

Martín, Judith; Merino, Isabel; Fanjul-Mosteirín, Noé; Mendoza, Rafael; García-Granda, Santiago; Concellón, Carmen; Amo, Vicente del

doi:10.1002/ejoc.201801509

Eur J Org Chem

2018

DOI: 10.1002/ejoc.201801509

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Unraveling the Role of Supramolecular Additives in a Proline‐Catalyzed Reaction

Judith Martín

Isabel Merino

Noé Fanjul-Mosteirín

et al.

Abstract: Various additives, typically based on molecules featuring H‐bond donor motifs, have been essayed towards improving the catalytic properties of proline. However, their mode of action is not clear yet. By employing in situ 1H and 19F NMR DOSY experiments, the role of a tetrafluoroborate guanidinium salt in a novel proline‐catalyzed cross‐aldol reaction between α,α‐dichloroacetone and aromatic aldehydes has been fully disclosed.

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2024

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Synergistic One‐pot Tandem Combination of Cu and Proline Catalysis: Stereodivergent Synthesis of Chiral Aldols from Primary Alcohols

López‐Aguilar,

Ramos‐Martín,

Ríos‐Lombardía

et al. 2024

ChemCatChem

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A new stereodivergent one‐pot tandem protocol, which granted diastereo‐ and enantioselective access to chiral aldols by starting from simple primary alcohols, is presented as a proof‐of‐concept. The synergistic combination of a chemoselective Cu(II)‐catalyzed oxidation of primary alcohols into the corresponding aldehydes (without the expected overoxidation into the corresponding carboxylic acids and using simple aerial O2 as co‐oxidant), followed by a concomitant organocatalyzed enantioselective aldol coupling promoted by the system (S)‐proline/HTBD‐BF4 [TBD = 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene], was achieved after fine‐tuning and compatibilizing the conditions required for the successful performance of both catalytic systems. Here, we demonstrated that selection and pairing of both catalysts needs to be extremely judicious to avoid orthogonality, kinetic, concentration or reciprocal poisoning issues. Refinement of the overall tandem protocol allowed us to design a synergistic and stereodivergent protocol which affords comparable or even better diastereoselective results than the organocatalytic system by itself. Finally, the following key factors (from a sustainable point of view) should be highlighted: i) no external VOC solvents are needed during our one‐pot tandem synthetic protocol (by working under neat conditions); and ii) isolation/purification of any intermediate is not required, thus reducing the chemical waste and energy/time costs, simplifying the practical aspects of our synthetic methodology

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Synergistic One‐pot Tandem Combination of Cu and Proline Catalysis: Stereodivergent Synthesis of Chiral Aldols from Primary Alcohols

López‐Aguilar,

Ramos‐Martín,

Ríos‐Lombardía

et al. 2024

ChemCatChem

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show abstract

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Unraveling the Role of Supramolecular Additives in a Proline‐Catalyzed Reaction

Cited by 1 publication

References 69 publications

Synergistic One‐pot Tandem Combination of Cu and Proline Catalysis: Stereodivergent Synthesis of Chiral Aldols from Primary Alcohols

Synergistic One‐pot Tandem Combination of Cu and Proline Catalysis: Stereodivergent Synthesis of Chiral Aldols from Primary Alcohols

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