L-Phenylglycine

CijH NO 21288-34-6) see Ketoprofen A -benzoyl-L-phenylglycinal (C15H15NO2 I630I0-72-8) see Paditaxel (2/ ,3S)-A -benzoyl-3-phenylisoserine (C H 5N04 132201-33-3) see Paditaxel (2i ,35)-A -benzoyl-3-phenylisoserine ethyl ester (Cii,HhjN04 153433-80-8) see Paditaxel 2-benzoylpyridine... 

FIG U RE 2.25 Stereo views of the complexes between (a) TAG and iV-acetyl-D-phenylgly cine or (c) iV-acetyl-L-phenylglycine, generated by computer modeling, (b) Exploded view of the complex between TAG and N-acetyl-phenylglycine (unspecified stereochemistry at the ligand). The primary amino group of TAG is converted to a ureido function to model the TAG CSP. 

The polarographic method has been used to determine the stability constants and kinetic parameters of ternary complexes of Zn(II) with L-lysine, L-omithine, L-serine, L-phenylglycine, L-phenylalanine, L-glutamic acid, and L-aspartic acid as primary ligands and picoline as secondary ligand at pH 8.5 [103] and also of zinc complexation by extracellular polymers extracted from activated sludge [104]. 

The key sequence in a somewhat involved stereospecihc total synthesis of a carbacephem starts by preparation of a chiral auxiliary. It is interesting to note that nitrogen is the only atom from this molecule retained in the hnal product. Constmction of this moiety starts with the formation of the carbethoxy derivative (37-2) from L(- -)-phenylglycine (37-1). Selective reduction of the free carboxyl group with borane. THF leads to the hydroxycarbamate (37-3). In a one-pot sequence, this is first cyclized to the corresponding oxazolidinone (37-4) by means of sodium hydride and then alkylated with ethyl bromoacetate (37-5). Saponification of the side chain then affords the chiral acetic acid (37-6). The carboxyl group is then activated by conversion to its acid chloride (37-7). 

A simple amino acid salt, sodium L-phenylglycinate, catalyses the enantioselective... 

S)-Phenyl-2-oxazolidinone.6 A one-pot route to this chiral auxiliary involves reduction of L-phenylglycine and BF3 etherate in DME with borane-dimethyl sulfide complex at a temperature maintained at 82°. The resulting phenylglycinol is then treated with trichloromethyl chloroformate (or the more expensive triphosgene). 

Similarly, fV-BOC-aminoalcohols can be subjected to Mitsunobu reaction conditions to yield the piperidine structure 10 (Equation 26) <2004JOC2229>, which is an intermediate in the synthesis of galactohomonojirimycin (BOC = /-butoxycarbonyl). Cyclization of an iV-BOC derivative of an aminoalcohol mesylate was reported in the synthesis of enantiopure 3-hydroxy-4-phenylpiperidine derivatives starting from L-phenylglycine <2004TL987>. 

Preparation of (S-(—)adamantane-l-phenylglycine hydrogen chloride salt... 

Lou, W.-Y., Zong, M.-H., Liu, Y.-Y., and Wang, J.-F. 2006. Efficient enantioselective hydrolysis of D,L-phenylglycine methyl ester catalyzed by immobilized Candida antarctica lipase B in ionic liquid containing systems. Journal of Biotechnology, 125 64—74. 

Cyclization of an allyl Af-acyl-l-phenylglycinate (398) with triphenylphosphine, hexa-chloroethane and triethylamine affords a 2-allyl-3-oxazolin-4-one (400) (81AG(E)395, 77AG(E)394). Reductive cleavage of the oxazolinone with chromium(II) acetate and aqueous hypophosphorous acid furnishes a jS,y-unsaturated ketone (Scheme 88). 

The synthesis of L-733,060 (1) using ring-closing metathesis starting from L-phenylglycine has been accomplished. 

Sarcosine, L-a-phenylsarcosine, L-phenylglycine, a-(2-iminohexa-hydro-4-pyrimidyl)-giycine... 

Asymmetric synthesis of a-methylene-y-lactams The organozinc reagents derived from 2-(bromomethyl)acrylates react with imines to form a-methylene-y-lactams. Use of (S)-l-phenylglycine as the chiral auxiliary for the imine provides these products in >95% ee. 

L-Phenylglycine and L-a-phenylalanine show in acid and in water a weak negative Cotton effect with a characteristic vibrational fine structure centered at 260 nm. In water, a strong positive Cotton effect is observed at 204 nm and a pronounced shoulder is seen at 214 nm, whereas in acidic solution the maximum occurs at 217 nm and the shoulder at 202 nm (Klyne et a/., 1971, and references therein). 

In the case of L-phenylalanine, in which the phenyl ring is separated from the center of asymmetry by a methylene group, the sign of the weak Cotton effect centered at 260 nm is reversed (as compared with that of L-phenylglycine) and is now positive there is also a much stronger positive Cotton effect of 217 nm at pH 1 (Verbit and Heffron, 1967, 1968). 

Takagi et a/., 1974), a-methyl-L-tyrosine (Goux et al, 1974), and p-hydroxy-L-phenylglycine (Snow and Hooker, 1974) have been studied by chiroptical means. 

Unlike the Cu(II) complexes of other L-amino acids, that of L-histidine yields a positive d-d Cotton effect. Also, on the basis of the CD spectra of L-proline, L-hydroxyproline, and L-phenylglycine amide complexes of Cu(II) and Ni(II), which show positive Cotton effects in the d-d transition region, the adequacy of the hexadecant rule has been questioned (Wellman et ai, 1969) together with the planar rule (C2h), quadrant rule (C2v), and octant rule (/>2h) The several sector rules have been compared and discussed by Martin (1974, pp. 129-156). 

Primary ammonium ions can bind to crown ethers, especially I8-crown-A derivatives, via formation of three H-bonds as shown in 5. In seminal work by Cram and coworkers, this interaction was exploited in a series of chiral receptors based on the twisted 1,1 -binaphthyl and 1,1-ditetralyI units. A key example is receptor 6, containing two binaphthyl units, of which one carries methyl substituents. This compound was capable of extracting protonated methyl d- and L-phenylglycinates and... 

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