Synthesis of 3-Unsubstituted 2-Hydroxy-4-oxoalkanoates

Meyer, Antoine; Flammang, M.; Wermuth, Camille‐Georges

doi:10.1055/s-1976-24229

Cited by 7 publications

(2 citation statements)

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“…Various methods have been utilized to prepare the remaining esters. For example, the 2-alkyl-4-aryl-2-hydroxybut-3-ynoate esters were prepared by reacting a terminal aryl acetylene with EtMgBr, followed by the appropiate ethyl 2-oxoalkanoate ester (eq 3) …”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2(3H)-Furanones via Electrophilic Cyclization

Just

Larock

2008

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 2(3H)-Furanones via Electrophilic Cyclization

Just

Larock

2008

J. Org. Chem.

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“…The nitrogen atom of amine 11 may be protected as the N -acetyl compound 50 , which was converted to the β-amino ketone 51 in a not-optimized 35% yield, after chromatographic purification . Also, the adduct 51 is a very attractive building block for the preparation of enantiomerically enriched, functionalized molecules, among which chiral 1,3-hydroxy-amino derivatives occupy a pre-eminent role.…”

Section: Resultsmentioning

confidence: 99%

Very Mild, Enantioselective Synthesis of Propargylamines Catalyzed by Copper(I)−Bisimine Complexes

et al. 2006

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The stereoselective addition of aryl- and alkylacetylene derivatives to imines was studied. The reaction is catalyzed by copper complexes of enantiomerically pure bisimines, readily prepared in very high yields from the commercially available binaphthyl diamine. A very simple experimental procedure allowed to obtain at room temperature optically active propargylamines in high yields and enantioselectivity. Interestingly, bisimine/copper(I) complexes were able to promote the direct, enantioselective, catalytic addition to imines of alkylacetylenes. The effects of catalyst loading and other reaction parameters on the stereochemical outcome of the transformation were investigated. The extremely convenient methodology, the mild reaction conditions, and the possibility of a modular approach for developing new and more efficient bisimine-based chiral ligands make the present methodology very attractive.

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Enantiocontrolled Synthesis of Tertiary α‐Hydroxy‐α‐ynyl Esters by Dimethylzinc‐Mediated Addition of Alkynes to α‐Keto Esters

et al. 2012

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A perhydro-1,3-benzoxazine behaves as an excellent chiral ligand in the nucleophilic addition of alkynylzinc derivatives, prepared from terminal alkynes and dimethylzinc, to a-keto esters without using other Lewis acids. The enantioselectivity is excellent and homogeneous for a wide variety of aromatic and heteroaromatic a-keto esters. Aliphatic enolizable a-keto esters were alkynylated with moderate enantioselection.

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Synthesis of 3-Unsubstituted 2-Hydroxy-4-oxoalkanoates

Cited by 7 publications

References 0 publications

Synthesis of 2(3H)-Furanones via Electrophilic Cyclization

Synthesis of 2(3H)-Furanones via Electrophilic Cyclization

Very Mild, Enantioselective Synthesis of Propargylamines Catalyzed by Copper(I)−Bisimine Complexes

Enantiocontrolled Synthesis of Tertiary α‐Hydroxy‐α‐ynyl Esters by Dimethylzinc‐Mediated Addition of Alkynes to α‐Keto Esters

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