Untitled

Valerio‐Alfaro, Gerardo; Garcı́a, Hugo S.; Luna, Héctor; Almanza, Raymundo Cruz

doi:10.1023/a:1005616824806

Cited by 9 publications

(1 citation statement)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The stereoselective synthesis of chiral 2-hydroxy amides include enzyme catalyzed reactions with α-oxo esters [12], one-pot asymmetric epoxidation of α,β-unsaturated amides followed by Pd-catalysed epoxide opening [13], from aldehydes by a bienzymatic cascade combining hydroxynitrile and nitrile hydratase [14], and reaction of the α-hydroxy esters with amines in the presence of Candida antarctica lipase [15]. Asymmetric reduction of α-keto amides for the steresoselective synthesis of 2-hydroxy amides were accomplished by hydrogenation with chiral Ru-[BINAP] complex [16], chiral CuII/(S)-DTBM-SEGPHOS catalyzed hydrosilylation [17], and organocatalytic Henry reactions using chiral bisoxazolidine and Cu(OTf) 2 [18].…”

Section: Introductionmentioning

confidence: 99%

A Mild and Eco-friendly, One-pot Synthesis of 2-hydroxy-Narylacetamides from 2-chloro-N-arylacetamides

Radhakrishna,

Khatik,

Vijaya

et al. 2024

LOC

View full text Add to dashboard Cite

A mild and eco-friendly one-pot, two-step procedure has been developed for the synthesis of 2-hydroxy-N-arylacetamides from 2-chloro-N-arylacetamides. The procedure overcomes the cleavage of the amide linkage in 2-chloroacetamides, which is usually observed under reflux conditions with the hydroxide when the nucleophilic substitution of the halide is attempted. The reactions were performed by refluxing 2-chloro-N-arylacetamides with Cu(OAc)2 and DIPEA in the ethanol medium to facilitate an acetate exchange with the halogen. Subsequently, by the addition of ethanolic KOH solution to the same reaction flask, the ester linkage was selectively cleaved in the presence of the amide, taking advantage of the difference in electrophilicity. The procedure afforded good yields of the desired products, which are valuable intermediates for several biologically active molecules, in a short reaction time with ease of isolation. The experimental conditions employed are simple and offer the possibility of scaling up to higher quantities.

show abstract

Section: Introductionmentioning

confidence: 99%

A Mild and Eco-friendly, One-pot Synthesis of 2-hydroxy-Narylacetamides from 2-chloro-N-arylacetamides

Radhakrishna,

Khatik,

Vijaya

et al. 2024

LOC

View full text Add to dashboard Cite

show abstract

Current Awareness

2000

Yeast

View full text Add to dashboard Cite

In order to keep subscribers up‐to‐date with the latest developments in their field, this current awareness service is provided by John Wiley & Sons and contains newly‐published material on yeasts. Each bibliography is divided into 10 sections. 1 Books, Reviews & Symposia; 2 General; 3 Biochemistry; 4 Biotechnology; 5 Cell Biology; 6 Gene Expression; 7 Genetics; 8 Physiology; 9 Medical Mycology; 10 Recombinant DNA Technology. Within each section, articles are listed in alphabetical order with respect to author. If, in the preceding period, no publications are located relevant to any one of these headings, that section will be omitted. (3 weeks journals ‐ search completed 21st June 2000)

show abstract

Synthesis of chiral α-hydroxy amides by two sequential enzymatic catalyzed reactions

Salinas

Oliart-Ros

Ramírez-Lepe

et al. 2007

Appl Microbiol Biotechnol

View full text Add to dashboard Cite

Enantiomerically pure alpha-hydroxy amides have been prepared from the corresponding alpha-oxo esters by the use of a double sequence reaction involving in a first step the highly enantioselective Saccharomyces cerevisiae bioreduction and then in a second step, the resulting alpha-hydroxy esters followed a non-enantiospecific lipase catalyzed aminolysis with n-butylamine reaction. In the first non-organic solvent process, the moistened baker's yeast reduced seven alpha-oxo esters with high conversions degree (93% for one substrate and >99% for the others) and high enantioselectivities [>99% for all the substrates except for ketopantoyl lactone, which gave 88% of enantiomeric excess (ee)]. At the same way, the isolated resulting chiral alpha-hydroxy esters were subjected to the second Candida antarctica lipase fraction B (CAL-B) catalyzed aminolysis in dioxane conducting to the corresponding chiral alpha-hydroxy amides with high conversions degree, between 88 and 99%. Both processes were carried out at 28-30 degrees C.

show abstract

Untitled

Cited by 9 publications

References 10 publications

A Mild and Eco-friendly, One-pot Synthesis of 2-hydroxy-Narylacetamides from 2-chloro-N-arylacetamides

A Mild and Eco-friendly, One-pot Synthesis of 2-hydroxy-Narylacetamides from 2-chloro-N-arylacetamides

Current Awareness

Synthesis of chiral α-hydroxy amides by two sequential enzymatic catalyzed reactions

Contact Info

Product

Resources

About