151436-20-3Relevant academic research and scientific papers
Synthesis of Unsaturated α-Amino Acids using the Ramberg-Baecklund Reaction
Guo, Zhao-Xia,Schaeffer, Marcel J.,Taylor, Richard J. K.
, p. 874 - 875 (1993)
A novel, and potentially versatile, procedure for the preparation of unsaturated α-amino acids in homochiral form is illustrated by the conversion of methionine into allylglycine (as its Boc, tert-butyl ester derivative) using the Ramberg-Baecklund reaction in the key step.
Total synthesis and absolute configuration of the natural amino acid tetrahydrolathyrine
Benohoud, Meryem,Leman, Loic,Cardoso, Silvia H.,Retailleau, Pascal,Dauban, Philippe,Thierry, Josiane,Dodd, Robert H.
supporting information; experimental part, p. 5331 - 5336 (2009/12/03)
(Chemical Equation Presented) The natural product tetrahydrolathyrine has been synthesized through an iminoiodane-mediated aziridination of a (2S)-allylglycinol derivative, which provided a 2:3 mixture of diastereoisomers. One of these diastereoisomers wa
Synthesis of isotopically labelled amino acids
Rees, David O.,Bushby, Nick,Harding, John R.,Song, Chuanjun,Willis, Christine L.
, p. 399 - 401 (2008/02/08)
An efficient approach to the enantioselective synthesis of a series of amino acids from either bromoacetyl bromide or glycine is described using a [2,3]-sigmatropic rearrangement to establish the stereogenic centre at C-2 under mild conditions. Protected allylglycine 5 is a valuable building block to several amino acids e.g. hydrolytic cleavage of the auxiliary in 5 followed by deprotection gave L-allylglycine in 92% yield whilst oxidative cleavage of the terminal alkene followed by deprotection gave L-aspartic acid in 67% yield over the 2 steps. Furthermore alkene 5 may be converted to hydroxy ester 8 which is an intermediate for the synthesis of various amino acids including L-lysine and L-proline. Since the enantiomer of sultam 1 is commercially available, the analogous D-amino acids may be synthesised. This chemistry is readily adapted for the incorporation of isotopic labels for example for the synthesis of [1,2-13C2,15N]-L-homoserine 14. Copyright
Synthesis of 5/7-, 5/8- And 5/9-bicyclic lactam templates as constraints for external β-turns
Duggan, Heather M. E.,Hitchcock, Peter B.,Young, Douglas W.
, p. 2287 - 2295 (2007/10/03)
The 5/7-, 5/8- and 5/9-bicyclic lactams 3, 17, 5 and 6 have been synthesised as single diastereoisomers by a route involving ring closing olefin metathesis. The X-ray crystal structure of the amino acid hydrochloride 17 has been carried out and compared t
Stereoselective synthesis of allyl- and homoallylglycines
Douat, Céline,Heitz, Annie,Martinez, Jean,Fehrentz, Jean-Alain
, p. 3319 - 3321 (2007/10/03)
A new method for the synthesis of N-protected allyl- and homoallylglycines was developed from aspartic and glutamic acid derivatives. The carboxylic side-chains of aspartic and glutamic derivatives was first transformed into the Weinreb amide by coupling with N,O-dimethylhydroxylamine and then reduced into the corresponding aldehyde. The latter could react with methyl-triphenylphosphonium bromide to yield the title compounds with 50% total yield.
Use of (S)-N-tert-butoxycarbonylaziridine-2-carboxylate derivatives for α-amino acid synthesis
Baldwin, Jack E.,Farthing, Christopher N.,Russell, Andrew T.,Schofield, Christopher J.,Spivey, Alan C.
, p. 3761 - 3764 (2007/10/03)
(S)-tert-Butyl-N-tert-butoxycarbonylaziridine-2-carboxylate and (S)-tert-butyl-N-tert-butoxycarbonylaziridine-2-carboxamide were synthesised and found to react with copper 'catalysed' Grignard reagents to give protected α-amino acids in moderate to good yields.
Enantioselective allylation of α-ketoester oximes with an external chiral ligand: Asymmetric synthesis of allylglycines and allylalanine
Hanessian, Stephen,Yang, Rui-Yang
, p. 8997 - 9000 (2007/10/03)
A highly enantioselective allylation of oximes of α-ketoesters is described with phenyl substituted chiral bis(oxazoline) as external ligand of allylzinc reagents. This method provides an efficient and convenient access to N-benzyloxy allylglycine, allylglycine and chain substituted variants with high enantiomeric purities. Copyright (C) 1996 Elsevier Science Ltd.
