Tuning the sense of product stereochemistry in aldol reactions of acetone and aromatic aldehydes in the presence of water with a single chiral catalyst

Gurka, András A.; Szőri, Kornél; Szőllősi, György; Bartók, Mihály; London, Gábor

doi:10.1016/j.tetlet.2015.11.051

Cited by 11 publications

(4 citation statements)

References 41 publications

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“…In the presence of ammonium chloride (R)-98 was obtained in 58% ee, whereas in the presence of NaOAc its enantiomer was formed in only 20% ee (Scheme 29). 102 This methodology was further studied with different aromatic aldehydes. 103 The formation of a biphasic micellar system in the aqueous media seems to be crucial for the observed enantioselectivities.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Stereodivergent Catalysis

2018

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This review covers diastereo- and enantiodivergent catalyzed reactions in acyclic and cyclic systems using metal complexes or organocatalysts. Among them, nucleophilic addition to carbon-carbon and carbon-nitrogen double bonds, α-functionalization of carbonyl compounds, allylic substitutions, and ring opening of oxiranes and aziridines are considered. The diastereodivergent synthesis of alkenes from alkynes is also included. Finally, stereodivergent intramolecular and intermolecular cycloadditions and other cyclizations are also reported.

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Section: Chemical Reviewsmentioning

confidence: 99%

Stereodivergent Catalysis

2018

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“…The reaction between acetone and cyclohexanone with 2-and 4-nitrobenzaldehyde gave the corresponding aldols with up to quantitative yields, but with low-to-medium enantiomeric excesses. Finally,i n2 015 London et al [34] reported the aldol reactionb etween acetonea nd aldehydes catalyzed by differente sters that incorporated (2S,4R)-4-hydroxyproline.T hese authors reported that, in the presence of water/ PPG425 (PPG425 = poly(propylene glycol)w ith averagem olecular weight of ca. 425) and NaOAc, preferential formation of the (S)-aldol was observedw ith low enantiomeric excesses( % 20 %), whereas with NH 4 Cl the corresponding (R)-enantiomers were obtained as major isomersw ith an ee value of approximately 58 %.…”

Section: Ester Derivativesmentioning

confidence: 99%

“…The reaction between acetone and cyclohexanone with 2‐ and 4‐nitrobenzaldehyde gave the corresponding aldols with up to quantitative yields, but with low‐to‐medium enantiomeric excesses. Finally, in 2015 London et al . reported the aldol reaction between acetone and aldehydes catalyzed by different esters that incorporated (2 S ,4 R )‐4‐hydroxyproline.…”

Section: Organocatalysts Derived From Post‐translational Amino Acidsmentioning

confidence: 99%

Organocatalysts Derived from Unnatural α‐Amino Acids: Scope and Applications

Agirre

Arrieta

Arrastia

et al. 2018

Chemistry An Asian Journal

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The organocatalytic properties of unnatural aamino acids are reviewed. Post-translational derivatives of natural a-aminoa cids include 4-hydroxy-l-proline and 4amino-l-proline scaffolds, and also prolineh omologues. The activity of synthetic unnatural a-amino acid-based organocatalysts, such as b-alkyl alanines, alanine-based phosphines, and tert-leucine derivatives, are reviewed herein. The orga-nocatalytic properties of unnatural monocyclic,b icyclic, and tricyclicproline derivatives are also reviewed. Severalfamilies of these organocatalystsp ermitthe efficient and stereoselective synthesis of complex natural products. Most of the reviewedo rganocatalysts accelerate the reported reactions through covalent interactions that raise the HOMO (enamine intermediates) or lower the LUMO (iminiumintermediates).Scheme1.Ageneral (simplified) mechanism of addition reactionsbye namine organocatalysis promoted by a-amino acid derivatives.[a] M.

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“…In the same year, the role of water in prolinecatalyzed aldol reactions was also reported by Ribas-Arino. 14 In 2015, London et al 15 developed aqueous aldol reactions of acetone with aromatic aldehydes, in which the sense of product stereochemistry was tuned with salt additives using L-hydroxyproline-based chiral catalysts 2-5 ( Figure 5). A transition state involving catalysts 2-5 in the presence of a large amount of water with NaOAc as an additive was proposed ( Figure 6).…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Recent Advances in Asymmetric Reactions Catalyzed by Proline and Its Derivatives

Liu

Wang

2016

Synthesis

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Asymmetric reactions are carried out by organocatalysis in many ways, making them very competitive and practical. One remarkable molecule, the amino acid proline, has become a crucial component in organocatalysis because of its ability to promote chemical transformations with high enantioselectivity. The following review discusses the contributions and recent advances in the field of asymmetric reactions catalyzed by L-proline and its derivatives. 1 Introduction 2 Asymmetric Aldol Reactions Catalyzed by Proline and Its Derivatives 2.1 Reactions of Ketones as Aldol Donors with Aldehydes as Aldol Acceptors 2.2 Reactions of Aldehydes as Aldol Donors with Aldehydes as Aldol Acceptors 2.3 Reactions of Aldehydes as Aldol Donors with Active Ketones as Aldol Acceptors 2.4 Reactions of Ketones as Aldol Donors with Active Ketones as Aldol Acceptors 3 Asymmetric Mannich Reactions Catalyzed by Proline and Its Derivatives 4 Asymmetric Michael Reactions Catalyzed by Proline and Its Derivatives 5 Asymmetric α-Amination Reactions Catalyzed by Proline and Its Derivatives 6 Conclusion

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Tuning the sense of product stereochemistry in aldol reactions of acetone and aromatic aldehydes in the presence of water with a single chiral catalyst

Cited by 11 publications

References 41 publications

Stereodivergent Catalysis

Stereodivergent Catalysis

Organocatalysts Derived from Unnatural α‐Amino Acids: Scope and Applications

Recent Advances in Asymmetric Reactions Catalyzed by Proline and Its Derivatives

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