Mandelic acid derived α-aziridinyl alcohols as highly efficient ligands for asymmetric additions of zinc organyls to aldehydes

Rachwalski, Michał; Jarzyński, Szymon; Jasiński, Marcin; Leśniak, Stanisław

doi:10.1016/j.tetasy.2013.04.019

Cited by 35 publications

(6 citation statements)

References 19 publications

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“…An easy access to both enantiomeric products using diastereomeric forms of the ligand was demonstrated. As a continuation of our interest in the field of asymmetric synthesis14–18 and taking all the aforementioned results into account, we have extended the scope of applicability of our heteroorganic tridentate ligands11 by checking them as catalysts for the asymmetric Simmons–Smith reaction of allylic alcohols. Notably, this is the first attempt at the use of these types of ligands in the asymmetric synthesis involving a carbenoid‐like intermediate.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Asymmetric Simmons–Smith Cyclopropanation Promoted by Chiral Heteroorganic Aziridinyl Ligands

et al. 2014

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Enantiomerically pure heteroorganic catalysts, bearing a hydroxy moiety, a stereogenic sulfinyl group, and a chiral aziridine moiety, have proved highly efficient in the asymmetric Simmons–Smith cyclopropanation of allylic alcohols, which generates the desired products in high yields (up to 95 %) and with ee values up to 94 %. The effect of the stereogenic centers at the sulfinyl sulfur atom and in the aziridine moiety on the stereochemical course of the title reaction is discussed.

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Section: Introductionmentioning

confidence: 99%

Highly Efficient Asymmetric Simmons–Smith Cyclopropanation Promoted by Chiral Heteroorganic Aziridinyl Ligands

et al. 2014

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“…Compound 2 was synthesized starting from ( S )-(+)-mandelic acid. The secondary alcohol of mandelic acid was acetylated, after which treatment with oxalyl chloride yielded 8 , which was reacted with 9 to afford 10 . , Finally, compound ( S )-(−)- 2 ( 2a ) was obtained by deacetylation of 10 (Scheme ). Using the same method, enantiomer ( R )-(+)- 2 ( 2b ) was also synthesized from ( R )-(+)-mandelic acid.…”

Section: Resultsmentioning

confidence: 99%

Penipyridones A–F, Pyridone Alkaloids fromPenicillium funiculosum

Zhou

et al. 2016

J. Nat. Prod.

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Six new pyridone alkaloids, named penipyridones A-F (1-6), were isolated from the fermentation broth of an Antarctic moss-derived fungus, Penicillium funiculosum GWT2-24. Their structures were elucidated from extensive NMR and MS data. Although they possess the same major chromophore and some of them presented almost mirror ECD spectra, their absolute configurations were found to be uniformly S, as evidenced by X-ray single-crystal diffraction analysis, stereocontrolled total synthesis, and chemical conversions. TDDFT-ECD calculations of compounds 3 and 6 revealed that subtle conformational changes are responsible for the significantly different ECD curves. None of the compounds were cytotoxic (IC50 > 50 μM), while compounds 1, 2, 5, and 7 elicited lipid-lowering activity in HepG2 hepatocytes.

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“…Saturated nitrogen-containing three-membered heterocycles have attracted increasing interest in recent years because compounds with this structural motif display quite diverse pharmacological activities. Chiral aziridines [51] also play an important role in asymmetric synthesis because they can act both as ligands [52][53][54][55] and as chiral auxiliaries [56]. The most widely used synthetic methods to form the aziridine ring [57][58][59][60][61] include intramolecular cyclizations in amines bearing potential leaving groups.…”

Section: Review Asymmetric Synthesis Of Aziridinesmentioning

confidence: 99%

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Mendes¹,

Costa²,

Yus³

et al. 2021

Beilstein J. Org. Chem.

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The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from tert-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format.

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Mandelic acid derived α-aziridinyl alcohols as highly efficient ligands for asymmetric additions of zinc organyls to aldehydes

Cited by 35 publications

References 19 publications

Highly Efficient Asymmetric Simmons–Smith Cyclopropanation Promoted by Chiral Heteroorganic Aziridinyl Ligands

Highly Efficient Asymmetric Simmons–Smith Cyclopropanation Promoted by Chiral Heteroorganic Aziridinyl Ligands

Penipyridones A–F, Pyridone Alkaloids fromPenicillium funiculosum

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

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