Asymmetric Synthesis of Chiral γ‐ and δ‐Amino Esters Using Trichlorosilane Activated with a Lewis Base Catalyst

Hasdemir, Belma; Yaşa, Hasniye; Yıldız, Tülay; Küçük, Hatice Başpınar; Onar, Hülya Çelik

doi:10.1002/slct.202000790

Cited by 4 publications

(2 citation statements)

References 55 publications

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“…Various amino acid–based molecules were tried in the aldolization reaction as organocatalysts in this study. Among the catalysts used, only l -proline ( 3a ), ( R )-amino-phenyl-acetic acid ( 3b ), and ( S )-diphenyl-pyrrolidin-2-yl-methanol ( 3c ) were purchased, while the others ( 3c - 3i ) were synthesized in our previous studies. , All amino acid-derived organocatalysts, except for l -proline, were used for the first time in an aldol reaction. These organocatalysts used are given in Figure , and the results obtained from these catalysts are shown in Table .…”

Section: Resultsmentioning

confidence: 99%

New Strategy for the Synthesis of Some Valuable Chiral 1,3-Diols with High Enantiomeric Purity: New Organocatalyst, Asymmetric Aldol Reaction, and Reduction

Yıldız,

Hasdemir,

Yaşa

et al. 2024

ACS Omega

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Chiral 1,3-diols are highly valuable molecules used in industries such as pharmaceuticals, cosmetics, and agriculture. Therefore, in this study, a new strategy was developed to synthesize enantiomerically pure (>99% ee) 1,3-diols. New chiral 1,3-diols (5a−5q) with high enantiomeric purity were synthesized from aldol products chiral 1,3-keto alcohols (4a−4q), which are aldol products with different structures. Chiral 1,3-keto alcohols (4a−4q) were synthesized by a new asymmetric aldol method in the first step. This method was developed using a new proline-derived organocatalyst (3g) and Cu(OTf) 2 as an additive in DMSO−H 2 O for the first time. Almost >99% ee was obtained using our developed aldol procedure. In the second step, original chiral diols (5a−5q) of high enantiomeric purity were obtained by asymmetric reduction of chiral keto alcohols with chiral oxazaborolidine reagents. In this way, a two-step asymmetric reaction was developed for chiral 1,3-diol enantiomers with high enantiomeric purity. The structures of all the original chiral compounds obtained were elucidated by infrared and nuclear magnetic resonance spectroscopy, mass spectrometry, and elemental analysis methods. Their enantiomeric excesses were determined by the chiral high-performance liquid chromatography method. Both keto alcohols and their corresponding chiral diols synthesized can be used as chiral starting materials and chiral source materials or intermediates in the synthesis of many biologically active molecules, or they can be used as chiral ligands in asymmetric synthesis, serving as organocatalysts.

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Section: Resultsmentioning

confidence: 99%

New Strategy for the Synthesis of Some Valuable Chiral 1,3-Diols with High Enantiomeric Purity: New Organocatalyst, Asymmetric Aldol Reaction, and Reduction

Yıldız,

Hasdemir,

Yaşa

et al. 2024

ACS Omega

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“…Very recently, Hasdemir et al . reported 24 a catalyzed asymmetric reduction of imino esters for the synthesis of chiral γ‐and δ‐amino esters [47] . High yields and good enantioselectivities were obtained.…”

Section: Asymmetric Reduction Using Silicon Hydrides Catalyzed By Chiral Lewis Basesmentioning

confidence: 98%

The Development of Organocatalytic Asymmetric Reduction of Carbonyls and Imines Using Silicon Hydrides

et al. 2021

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The asymmetric reduction of prochiral ketones and ketimines represents one of the most important and practical chemical transformations toward the synthesis of valuable chiral alcohols and amines. Among the existing strategies, organocatalyzed asymmetric reduction of carbonyls and imines using silicon hydrides is attractive due to low-cost, chemical stability, and easy handling in experiments. In this review, we wish to highlight the recent progress made in the past fifteen years in this field. Four catalytic systems of different activation modes are presented and discussed in detail. We aim to help shed light on common features that enable highly enantioselective silicon hydride reductions through organocatalysis and provide the design principles for the development of more effective catalytic systems.

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Effect of the acyl-group length on the chemoselectivity of the lipase-catalyzed acylation of propranolol—a computational study

2021

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Asymmetric Synthesis of Chiral γ‐ and δ‐Amino Esters Using Trichlorosilane Activated with a Lewis Base Catalyst

Cited by 4 publications

References 55 publications

New Strategy for the Synthesis of Some Valuable Chiral 1,3-Diols with High Enantiomeric Purity: New Organocatalyst, Asymmetric Aldol Reaction, and Reduction

New Strategy for the Synthesis of Some Valuable Chiral 1,3-Diols with High Enantiomeric Purity: New Organocatalyst, Asymmetric Aldol Reaction, and Reduction

The Development of Organocatalytic Asymmetric Reduction of Carbonyls and Imines Using Silicon Hydrides

Effect of the acyl-group length on the chemoselectivity of the lipase-catalyzed acylation of propranolol—a computational study

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