Straightforward synthesis of functionalized (E)-3-acylacrylic acids

Sivák, Ivan; Vaclav, Jakub; Berkeš, Dušan; Kolarovič, Andrej

doi:10.1016/j.tet.2015.10.003

Cited by 7 publications

(4 citation statements)

References 61 publications

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“…( S )-Citronellol (ee 95%), ( S )-1-phenylethylamine (ee 98%), and l -phenylglycinamide (ee 98%) were used as chiral building blocks. ( E )-3-Acylacrylic acids 3a , b , g–k were prepared following known procedures …”

Section: Methodssupporting

confidence: 89%

“…The crude product was crystallized from n -heptane, affording 827 mg (67%) of acid 3c as a white solid. 1 H NMR spectrum of the product was in a full agreement with the recently published data …”

Section: Methodsmentioning

confidence: 99%

“…Perhaps this might be attributed to the fact that, if variously functionalized, these were not readily obtainable for a long time. Recently, we have described their straightforward synthesis based on Horner–Wadsworth–Emmons reactions of a free glyoxylic acid, thus removing this hindrance . Herein, we report aza -Michael additions of diversely functionalized ( E )-3-acylacrylic acids as a synthetic platform for obtaining CIDT products in a well predictable fashion.…”

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confidence: 99%

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Stereoselective Synthesis of Functionalized α-Amino Acids Isolated by Filtration

et al. 2018

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Crystallization-induced diastereomer transformation (CIDT) represents a highly appealing and convenient synthetic tool. Despite its numerous advantages, it remains rather rarely used due to its uncertain predictability to occur. Herein, we describe CIDT based on aza-Michael reactions of diversely functionalized (E)-3-acylacrylic acids. This method provides direct access to a broad variety of α-amino acid derivatives in excellent stereochemical purities.

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Section: Methodssupporting

confidence: 89%

Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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Stereoselective Synthesis of Functionalized α-Amino Acids Isolated by Filtration

et al. 2018

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“…As β‐acylacrylic acids with functionalized aliphatic chains became readily available via a direct Horner‐Wadsworth‐Emmons reaction of glyoxylic acid, [115] the substrate scope for CIDT could be remarkably extended (Scheme 49C) [103] . Indeed, diverse functional groups were very well tolerated and provided the corresponding amino acids 133 l – p in fair yields and drs.…”

Section: Examples Of Cidtmentioning

confidence: 99%

State of the Art in Crystallization‐Induced Diastereomer Transformations

Kolarovič

Jakubec

2021

Adv Synth Catal

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Crystallization-induced diastereomer transformations (CIDT) enable isolation of the target compounds in high enantio-and diastereomeric purities and with up to quantitative yields simply by filtration. Numerous inspiring examples of this appealing synthetic strategy reported over the last fifteen years are reviewed. Important observations along with aspects to consider when designing CIDT experiments are discussed. 3.3. Formation of Schiff Base or Related Intermediates 3.4. Aza-Michael and Mannich-Type Reactions 3.5. Strecker Reaction 3.6. Aldol Reactions 3.7. Epimerization at Phosphorus-Based Stereocenters 3.8. Racemization/Epimerization through Change of Conformation 3.9. Miscellaneous Examples of CIDT 4.Conclusions and Perspectives

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ChemInform Abstract: Straightforward Synthesis of Functionalized (E)‐3‐Acylacrylic Acids.

et al. 2016

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Straightforward Synthesis of Functionalized (E)-3-Acylacrylic Acids. -Starting from various carboxylic acid esters an efficient two-step route to (E)-3-acylacrylic acids via the corresponding ketophosphonates is developed. The method is applicable to esters deriving from primary, secondary, and tertiary carboxylic acids as well as lactones and cyclic anhydrides, and the substrates may contain diverse functional groups. -(SIVAK, I.; VACLAV, J.; BERKES, D.; KOLAROVIC*, A.; Tetrahedron 71 (2015) 47, 8876-8884, http://dx.

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Straightforward synthesis of functionalized (E)-3-acylacrylic acids

Cited by 7 publications

References 61 publications

Stereoselective Synthesis of Functionalized α-Amino Acids Isolated by Filtration

Stereoselective Synthesis of Functionalized α-Amino Acids Isolated by Filtration

State of the Art in Crystallization‐Induced Diastereomer Transformations

ChemInform Abstract: Straightforward Synthesis of Functionalized (E)‐3‐Acylacrylic Acids.

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