145513-90-2Relevant articles and documents
Versatile methodology for the synthesis and α-functionalization of (2R,3aS,7aS)-octahydroindole-2-carboxylic acid
Sayago, Francisco J.,Isabel Calaza,Jiménez, Ana I.,Cativiela, Carlos
, p. 84 - 91 (2008)
An improved strategy for the effective synthesis of enantiomerically pure (2R,3aS,7aS)-octahydroindole-2-carboxylic acid (Oic), based on the?formation of a trichloromethyloxazolidinone derivative, has been developed. Additionally, the completely diastereoselective α-alkylation of such oxazolidinone provides a very convenient and concise route to enantiopure α-tetrasubstituted derivatives of this Oic stereoisomer.
Practical access to the proline analogs (S,S,S)- and (R,R,R)-2- methyloctahydroindole-2-carboxylic acids by HPLC enantioseparation
Sayago, Francisco J.,Pueyo, Maria J.,Calaza, M. Isabel,Jimenez, Ana I.,Cativiela, Carlos
scheme or table, p. 507 - 513 (2012/01/11)
An efficient methodology for the preparation of the α- tetrasubstituted proline analog (S,S,S)-2-methyloctahydroindole-2-carboxylic acid, (S,S,S)-(αMe)Oic, and its enantiomer, (R,R,R)-(αMe)Oic, has been developed. Starting from easily available substrates and through simple transformations, a racemic precursor has been synthesized in excellent yield and further subjected to HPLC resolution using a cellulose-derived chiral stationary phase. Specifically, a semipreparative (250 mm × 20 mm ID) Chiralpak IC column has allowed the efficient resolution of more than 4 g of racemate using a mixture of n-hexane/tert-butyl methyl ether/2-propanol as the eluent. Multigram quantities of the target amino acids have been isolated in enantiomerically pure form and suitably protected for incorporation into peptides.
Efficient access to N-protected derivatives of (R,R,R)- and (S,S,S)-octahydroindole-2-carboxylic acid by HPLC resolution
Sayago, Francisco J.,Jimenez, Ana I.,Cativiela, Carlos
, p. 2358 - 2364 (2008/02/12)
The preparation of the proline analogue (2S,3aS,7aS)-octahydroindole-2-carboxylic acid (Oic) and its enantiomer, (2R,3aR,7aR)-Oic, is described. A racemic precursor has been synthesized in good yield and subjected to HPLC resolution on a chiral column. The high efficiency of both the synthetic and chromatographic procedures has allowed the isolation of multigram quantities of each amino acid in enantiomerically pure form and suitably protected for use in peptide synthesis.
SYNTHESIS OF 2S, 3aS, 7aS- AND OF 2S, 3aR, 7aR- PERHYDROINDOLE-2-CARBOXYLIC ACID DERIVATIVES FROM L-ASPARTIC ACID
Barton, Derek H. R.,Guilhem, Jean,Herve, Yolande,Potier, Pierre,Thierry, Josiane
, p. 1413 - 1416 (2007/10/02)
Using carbon radicals generated by photolysis of N-hydroxy-2-thio-pyridone esters (mixed anhydrides) the chiral centre of L-aspartic acid has been easily incorporated into the perhydroindole structure of the title compounds.
DIASTEREOSELECTIVE SYNTHESIS OF BICYCLIC AMINO ACIDS VIA RING CONTRACTION OF α-CHLOROLACTAMS
Henning, R.,Urbach, H.
, p. 5339 - 5342 (2007/10/02)
Bicyclic lactams were converted to their α-chloro-derivatives and subjected to ring contraction under basic conditions to give bicyclic acids in diasteroselective fashion.
COUPLING OF β-ACETAMIDO RADICALS WITH α-CHLORO ACRYLONITRILE - A NEW ACCESS TO DISUBSTITUTED PROLINE DERIVATIVES
Henning, R.,Urbach, H.
, p. 5343 - 5346 (2007/10/02)
β-Acetamido radicals are prepared by reduction of organomercurials and coupled with α-chloro-acrylonitrile.The coupling products are further converted to proline derivatives.
