Absolute configuration of (+)-1-amino-1-methylpropylphosphonic acid

Chekhlov, A. N.; Belov, Yu. P.; Мартынов, И. В.; Aksinenko, А. Yu.

doi:10.1007/bf01474236

Cited by 4 publications

(1 citation statement)

References 5 publications

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“…For crystal structures of R,R-tartaric mono amides, see: Rychlewska et al (1999); Rychlewska & Warżajtis (2000, 2001. For examples of the crystal structures of monoacyl derivatives, see: Madura et al (2010); Knyazev et al (1988); Chekhlov et al (1986); Ishihara et al (1993). For the synthesis, see: Bell (1987); Bernaś et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

(2R,3R)-3-O-Benzoyl-N-benzyltartramide

Madura¹,

Zachara²,

Bernaś³

et al. 2012

Acta Cryst E

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The title compound, C18H17NO6 [systematic name: (2R,3R)-4-benzylamino-2-benzoyloxy-3-hydroxy-4-oxobutanoic acid], is the first structurally characterized unsymmetrical monoamide–monoacyl tartaric acid derivative. The molecule shows a staggered conformation around the tartramide Csp3—Csp3 bond with trans-oriented carboxyl and amide groups. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, molecules are linked by O—H⋯O hydrogen bonds between the carboxyl and amide carbonyl groups, forming translational chains along [001]. Further O—H⋯O and N—H⋯O hydrogen bonds as well as weaker C—H⋯O and C—H⋯π intermolecular interactions extend the supramolecular assembly into a double-layer structure parallel to (100). There are no directional interactions between the double layers.

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Section: Related Literaturementioning

confidence: 99%

(2R,3R)-3-O-Benzoyl-N-benzyltartramide

Madura¹,

Zachara²,

Bernaś³

et al. 2012

Acta Cryst E

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The Synthesis of Functionalized Phosphinic and Phosphonic Acids and their Derivatives. PartB: Diazo, Nitro and Amino Functionalized Acids

Edmundson¹

2009

Patai's Chemistry of Functional Groups

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Preparation of α‐Aminobenzylphosphonic Acids with a Stereogenic Quaternary Carbon Atom via Microscopically Configurationally Stable α‐Aminobenzyllithiums

Kuliszewska

Hanbauer

Hammerschmidt

2008

Chemistry A European J

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The enantiomers of 1-phenylethylamine were phosphorylated with diethyl chlorophosphate/Et(3)N and then Boc-protected (Boc=tert-butoxycarbonyl) at the nitrogen atom. These phosphoramidates were metalated by using sBuLi/N,N,N',N'-tetramethylethylenediamine (TMEDA) to give alpha-aminobenzyllithiums that isomerised to alpha-aminophosphonates in yields of up to 80 % with retention of the configuration at the carbon atom. The intermediate tertiary organolithiums were found to be microscopically configurationally stable from -78 to 0 degrees C in Et(2)O. The protected alpha-aminophosphonates were deblocked by using boiling 6 M HCl or preferably Me(3)SiBr/(allyl)SiMe(3). When the Boc group was replaced by the diethoxyphosphinyl group, the alpha-aminobenzyllithium intermediate partially enantiomerised even at -78 degrees C and rearranged to yield an alpha-aminophosphonate with 50 % ee (ee=enantiomeric excess). Similarly, N-Boc-protected phosphoramidates derived from racemates and/or enantiomers of 1-(1-naphthyl)ethyl-, 1-indanyl- and 1,2,3,4-tetrahydro-1-naphthylamine or 1-azidoindan- and 1-azido-1,2,3,4-tetrahydronaphthalene were converted to aminophosphonates in good yields. Deblocking gave alpha-aminophosphonic acids of excellent enantiomeric excess (97-99 %), as determined by means of HPLC on a chiral ion-exchange stationary phase based on quinine carbamate. When racemic Boc-protected diethyl phosphoramidate derived from 1,2,3,4-tetrahydro-1-naphthylamine was metalated with LiTMP/TMEDA (TMP=2,2,6,6-tetramethylpiperidine), 1-hydroxyethylphosphonamidates resulted. The configuration of the main isomer was determined by means of a single-crystal X-ray structure analysis.

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Absolute configuration of (+)-1-amino-1-methylpropylphosphonic acid

Cited by 4 publications

References 5 publications

(2R,3R)-3-O-Benzoyl-N-benzyltartramide

(2R,3R)-3-O-Benzoyl-N-benzyltartramide

The Synthesis of Functionalized Phosphinic and Phosphonic Acids and their Derivatives. PartB: Diazo, Nitro and Amino Functionalized Acids

Preparation of α‐Aminobenzylphosphonic Acids with a Stereogenic Quaternary Carbon Atom via Microscopically Configurationally Stable α‐Aminobenzyllithiums

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