Reactions of Amines. XV. Synthesis of α-Amino Acids from Imino Esters<sup>1,2</sup>

Baumgarten, Henry E.; Dirks, Jerald E.; Petersen, James M.; Zey, Robert L.

doi:10.1021/jo01349a051

Cited by 15 publications

(1 citation statement)

References 3 publications

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“…The residue was chromatographed on two loose layers of silica gel (35 X 15 cm, 3 mm thick) in solvent SB containing 0.2% of triethylamine (double development). The faster moving band was eluted with the solvent and evaporated to give amorphous product 18b (0.185 g, 21%): TLC (S2) homogeneous; uv max (ethanol) 265 nm (£ 16 500), min 228 (2100); NMR (CD3COCD3 + D20) 8.15 (s, 2, Hg + H2), 7.13 (m, 10, C6Hb), 6.35 (d, 1, J = 3.5 Hz, Hr), 1.10 and 1.42 (two t, CH3 ofC2H60).…”

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confidence: 99%

Some transformations of DL-phenylalanine ortho esters and N-benzyloxycarbonyl-L-phenylalaninal

Zemlicka¹,

Murata²

1976

J. Org. Chem.

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Glycine ortho esters have found a wide use2 in the synthesis of glycyl derivatives of ribonucleosides,2a'b ribonucleotides,20 and ribooligonucleotides.2d_h The application of the ortho ester exchange method which provides the basis of the synthetic approach28 to the above mentioned compounds for amino acids other than glycine has been hampered for a long time by a lack of general method for the preparation of amino acid ortho esters.3

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Some transformations of DL-phenylalanine ortho esters and N-benzyloxycarbonyl-L-phenylalaninal

Zemlicka¹,

Murata²

1976

J. Org. Chem.

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Synthesis of [1-13C] and [1-15N] labelled DL-homophenylalanine via a key Neber rearrangement

Oldfield

Botting

1998

J Label Compd Radiopharm

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A synthetic route involving a key Neber rearrangement is described for the preparation of both [1‐13C] and [1‐15N] DL‐homophenylalanine (2‐amino‐4‐phenylbutanoic acid), using suitably labelled sodium cyanide as the source of the isotopic label. These compounds have been prepared for use in studies on the biosynthesis of phenylethyl glucosinolate in Brassica napus. 3‐Phenylpropanaldoxime, the initial biosynthetic product formed from homophenylalanine, was also prepared in 15N labelled form. © 1998 John Wiley & Sons, Ltd.

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syn‐anti Isomerizations and rearrangements

Mccarty

1970

PATAI'S Chemistry of Functional Groups

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Reactions of Amines. XV. Synthesis of α-Amino Acids from Imino Esters^1,2

Cited by 15 publications

References 3 publications

Some transformations of DL-phenylalanine ortho esters and N-benzyloxycarbonyl-L-phenylalaninal

Some transformations of DL-phenylalanine ortho esters and N-benzyloxycarbonyl-L-phenylalaninal

Synthesis of [1-13C] and [1-15N] labelled DL-homophenylalanine via a key Neber rearrangement

syn‐anti Isomerizations and rearrangements

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Reactions of Amines. XV. Synthesis of α-Amino Acids from Imino Esters1,2

Cited by 15 publications

References 3 publications

Some transformations of DL-phenylalanine ortho esters and N-benzyloxycarbonyl-L-phenylalaninal

Some transformations of DL-phenylalanine ortho esters and N-benzyloxycarbonyl-L-phenylalaninal

Synthesis of [1-13C] and [1-15N] labelled DL-homophenylalanine via a key Neber rearrangement

syn‐anti Isomerizations and rearrangements

Contact Info

Product

Resources

About

Reactions of Amines. XV. Synthesis of α-Amino Acids from Imino Esters^1,2