Journal ArticleDOI
Synthesis of enantiomerically pure aminophosphonic acids
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TLDR
An efficient general asymmetric synthesis of α-aminophosphonic acid derivatives has been achieved by alkylation of the Schiff bases 2, prepared from (1R,2R, 5R)(+) or (1S,2S, 5S)(-) 2-hydroxy 3-pinanone 1 and α -aminomethyl phosphonic acid diethylester.Abstract:
An efficient general asymmetric synthesis of α-aminophosphonic acid derivatives has been achieved by alkylation of the Schiff bases 2, prepared from (1R,2R, 5R)(+) or (1S,2S, 5S)(-) 2-hydroxy 3-pinanone 1 and α-aminomethyl phosphonic acid diethylester. Diastereoisomeric alkylated Schiff bases separated on column chromatography afforded after hydrolytic cleavage enantiomerically pure compounds.read more
Citations
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Synthetic methods for azaheterocyclic phosphonates and their biological activity.
Journal ArticleDOI
Asymmetric Synthesis of Phosphorus Analogs of Amino Acids
TL;DR: In this paper, the authors summarized data available in literature on asymmetric synthesis of phosphorus analogs of amino acids and arranged them according to the type of bond formation during a chiral center creation.
Journal ArticleDOI
A versatile asymmetric synthesis of α-amino α-alkyl-phosphonic acids of high enantiomeric purity
TL;DR: In this article, a general protocol for the synthesis of α-amino-α- alkyl phosphonic acids in either enantiomeric form is described based on the alkylation of chiral bicyclic phosphonamides derived from ( R,R )- and ( S,S )-1,2-diaminocyclohexane.
Journal ArticleDOI
Asymmetric Synthesis of Aziridine 2-Phosphonates from Enantiopure Sulfinimines (N-Sulfinyl Imines). Synthesis of α-Amino Phosphonates
TL;DR: An aza-Darzens reaction, involving the addition of chloromethylphosphonate anions to enantiopure sulfinimines, has been developed for the asymmetric synthesis of aziridine 2-ph phosphonates and results involve cyclization of the syn and anti diastereomerically pure alpha-chloro-beta-aminoosphonates to cis- and trans-N-sulfinyl azirids.
Journal ArticleDOI
The asymmetric synthesis of α-substituted α-methyl and α-phenyl phosphonic acids: Design, carbanion geometry, reactivity and preparative aspects of chiral alkyl bicyclic phosphonamides
TL;DR: In this article, the design, preparation, structural and spectroscopic analyses of topologically unique and enantiomerically pure alkyl phosphonamides are described and the geometry of both secondary and tertiary carbanions is determined through deprotonation/deuteration/alkylation experiments.
References
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Synthesis of an optically active -aminophosphonic acid.
Gilmore Wf,McBride Ha +1 more
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Synthesis and stereochemistry of the four isomeric pinane-2,3-diols
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Synthese asymetrique d'acides amines α-disubstitues
TL;DR: In this paper, the configuration of α-disubstituted amino acids is found to be dependent on the shielding effect of their aliphatic chain in the intermediary Schiff base dianion.
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Total synthesis of β-lactam antibiotics I.
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A general and accurate nmr determination of the enantiomeric purity of α-aminoacids and α-aminoacid derivatives
TL;DR: In this paper, the enantiomeric purity of α-aminoacids and α-aminolactones is determined using N-acetyl derivatives, and the major coordination site with a chiral shift reagent will correspond to the NMR observation site.