Synthesis of Enantiopure 1-Arylprop-2-en-1-ols and Their <i>tert</i>-Butyl Carbonates

Štambaský, Jan; Malkov, Andrei V.; Kočovský, Pavel

doi:10.1021/jo801874r

Cited by 30 publications

(26 citation statements)

References 23 publications

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“…Based on the above evidence, the planar structure of 1 was determined. The absolute configuration of 1 was determined to be aS by comparison of the optical rotation with the literature data [8], which was further confirmed by computational methods via calculation of the optical rotation values at three different levels (theory-B3LYP, B3P86, and PBE1PBE) using the 6-311 þ þ G(2d, p) and aug-cc-pVDZ basis set in the Gaussian 09 software [9,10] ( Table 2). The calculated specific rotation values and the experimental data for 1 were summarized in Table 2.…”

Section: Resultssupporting

confidence: 62%

A new phenylpropanoid and a new isoflavone glycoside from Shenqi Fuzheng Injection

Zhang

Fan

Huang

et al. 2014

Journal of Asian Natural Products Research

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A new phenylpropanoid and a new isoflavone glycoside were isolated from Shenqi Fuzheng Injection. Their structures were elucidated as (αS)-α-ethenyl-4-hydroxy-3-methoxy-benzenemethanol (1) and calycosin 7-O-[α-d-glucopyranosyl (1 → 4)]-β-d-glucopyranoside (2) by means of spectroscopic methods including UV, IR, HR-ESI-MS, and NMR. The absolute configurations of 1 and 2 were confirmed by quantum chemical calculation and acid hydrolysis.

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Section: Resultssupporting

confidence: 62%

A new phenylpropanoid and a new isoflavone glycoside from Shenqi Fuzheng Injection

Zhang

Fan

Huang

et al. 2014

Journal of Asian Natural Products Research

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“…Accordingly, the enantiopure allylic alcohol 27 [ 35 ] was extended through a cross-metathesis reaction to deliver the disubstituted alkene 30 ( Scheme 3 ). Compound 30 became the substrate for an attempted Sharpless asymmetric epoxidation reaction using (+)-DET ( Scheme 3 ); however, none of the desired product 28a was observed in this case, presumably due to a substrate/catalyst mismatch effect.…”

Section: Resultsmentioning

confidence: 99%

Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

Cheerlavancha¹,

Ahmed²,

Leung³

et al. 2017

Beilstein J. Org. Chem.

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Backbone-extended amino acids have a variety of potential applications in peptide and protein science, particularly if the geometry of the amino acid is controllable. Here we describe the synthesis of δ-amino acids that contain three vicinal C–F bonds positioned along the backbone. The ultimately successful synthetic approach emerged through the investigation of several methods based on both electrophilic and nucleophilic fluorination chemistry. We show that different diastereoisomers of this fluorinated δ-amino acid adopt distinct conformations in solution, suggesting that these molecules might have value as shape-controlled building blocks for future applications in peptide science.

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“…The recovered enantioenriched carbonates ( S )‐ 1 proved to be suitable substrates for stereospecific substitution in the presence of 2 and an iridium catalyst derived from achiral ligand L2 (Scheme ) providing optically active amide adducts ( S )‐ 3 (Scheme ) . All allylic carbonates underwent stereospecific substitution with high enantiospecificity (>93 % es ) and good yields.…”

Section: Methodsmentioning

confidence: 99%

Morpholine Ketene Aminal as Amide Enolate Surrogate in Iridium‐Catalyzed Asymmetric Allylic Alkylation

et al. 2019

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Morpholine ketene aminal is employed in iridiumcatalyzedasymmetric allylic alkylation reactions as asurrogate for amide enolates to prepare g,d-unsaturated b-substituted morpholine amides.Kinetic resolution or,alternatively,stereospecific substitution affords the corresponding products in high enantiomeric excess.T he utility of the products generated by this method has been showcased by their further elaboration into amines,k etones,o ra cyl silanes.Ap utative catalytic intermediate (h 3 -allyl)iridium(III) with achiral P, Olefin-ligand was synthetized and characterized for the first time.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Synthesis of Enantiopure 1-Arylprop-2-en-1-ols and Their tert-Butyl Carbonates

Cited by 30 publications

References 23 publications

A new phenylpropanoid and a new isoflavone glycoside from Shenqi Fuzheng Injection

A new phenylpropanoid and a new isoflavone glycoside from Shenqi Fuzheng Injection

Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

Morpholine Ketene Aminal as Amide Enolate Surrogate in Iridium‐Catalyzed Asymmetric Allylic Alkylation

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