58610-42-7Relevant academic research and scientific papers
Synthesis of β-amino acids based on oxidative cleavage of dihydropyridone derivatives
Ege, Markus,Wanner, Klaus T.
, p. 3553 - 3556 (2004)
(Chemical Equation Presented) A new method for the synthesis of β-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NaIO4 and subsequently with base gave the corresponding β-amino acids in a one-pot procedure. The reactions have been monitored by 1H NMR indicating that the β-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.
Towards a greener synthesis of (S)-3-aminobutanoic acid: Process development and environmental assessment
Weiss, Markus,Brinkmann, Tobias,Groeger, Harald
supporting information; experimental part, p. 1580 - 1588 (2010/12/19)
An improved, greener process for the enantioselective chemoenzymatic synthesis of (S)-3-aminobutanoic acid has been developed. Reaction steps comprise an initial aza-Michael addition starting from cheap prochiral compounds, subsequent enzymatic resolution via aminolysis using commercially available Candida antarctica lipase B in a solvent-free one-pot process, hydrolysis of the resulting ester and removal of the N-benzyl moiety via hydrogenation. After isolation, the desired (S)-3-aminobutanoic acid was obtained in an overall yield of 28% and with an excellent enantiomeric excess of 99% ee. Notably, this reaction sequence does not require column chromatography with organic solvents and only one purification step of an intermediate is needed. The environmental impact of this optimized process has been evaluated and an E-factor of 41 has been calculated for the overall process. A comparative assessment with the previous process was done via mass balancing using the E-factor, the selectivity index S-1 as well as an SHE assessment.
Practical, highly enantioselective chemoenzymatic one-pot synthesis of short-chain aliphatic β-amino acid esters
Wei?, Markus,Gr?ger, Harald
experimental part, p. 1251 - 1254 (2009/09/06)
A practical, highly enantioselective method for the synthesis of short-chain aliphatic β-amino acid esters was developed starting from prochiral and easily accessible substrates. This chemoenzymatic approach is based on a nonenzymatic aza-Michael addition
Diastereoselective synthesis of α-methyl and α-hydroxy-β- amino acids via 4-substituted-1,3-oxazinan-6-ones
Sleebs, Brad E.,Hughes, Andrew B.
, p. 3340 - 3352 (2008/02/08)
(Chemical Equation Presented) 1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3- oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazin
New access to racemic β3-amino acids
Nejman, Micha?,?liwińska, Anna,Zwierzak, Andrzej
, p. 8536 - 8541 (2007/10/03)
A general simple procedure having the potential for large scale preparations of racemic β3-amino acids has been developed. The procedure involves base-catalyzed Michael-type addition of sodium diethyl malonate to N-Boc-α-amidoalkyl-p-tolyl sulfones in tetrahydrofuran. Hydrolysis of the adducts by refluxing with 6 M aqueous hydrochloric acid affords β3-amino acid hydrochlorides in high yield and excellent purity.
Methods and compositions to protect crops against plant parasitic nematodes
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, (2008/06/13)
A method for protecting a crop against plant-parasitic nematode attack by inducing local and systemic resistance of the crop comprising the application of a composition containing an effective amount of β-amino butyric acid or derivatives thereof to the c
Method for protecting plants from fungal infection
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, (2008/06/13)
A method for protecting a crop against fungal diseases by inducing local and systemic resistance of the crop comprising applying to the crop or its locus a composition containing an effective amount of at least one β-aminobutyric acid or β-amino valeric a
Method to protect plants from fungal infection
-
, (2008/06/13)
A method for protecting a crop against fungal diseases by inducing local and systemic resistance of the crop comprising applying to the crop or its locus a composition containing an effective amount of a β-aminobutyric acid or β-amino valeric acid and der
The directed cleavage of substituted 1-phenylethylamines: A novel route to enantiomerically pure β-amino acid esters and β-lactams
Bringmann,Geuder
, p. 829 - 831 (2007/10/02)
An efficient novel access to enantiomerically pure β-amino acid esters and β-lactams (e.g., methyl (3S,4S)-1-(tert-butyldimethylsilyl-4-methyl-2-oxoazetidine-3-carboxylat e) from optically active 1-arylethylamines is described. Regiospecific cleavage is performed by Birch reduction and subsequent ozonolysis.
