145438-94-4Relevant articles and documents
The synthesis of trans-perhydroindolic acids and their application in asymmetric domino reactions of aldehyde esters with β,γ-unsaturated α-keto esters
Shen, Jiefeng,Liu, Delong,An, Qianjin,Liu, Yangang,Zhang, Wanbin
, p. 3311 - 3325 (2012)
(2S,3aR,7aS)-Perhydroindolic acid, the key intermediate in the synthesis of trandolapril, and its trans-isomers, were readily prepared. These proline-like molecules are unique in that they contain a rigid bicyclic structure, with two hydrogen atoms trans to each other at the bridgehead carbon atoms. These molecules were used successfully as chiral organocatalysts in asymmetric domino Michael addition/cyclization reactions of aldehyde esters with β,γ-unsaturated α-keto esters. They proved to have excellent catalytic behavior, allowing for the synthesis of multi-substituted, enantiomerically enriched hemiacetal esters. Under optimal conditions (using 10 mol% catalyst loading), a series of β,γ-unsaturated α-keto esters was examined with up to 99% de, ee and yield, respectively. Additionally, the enantiomerically enriched hemiacetal esters could be readily transformed into their corresponding bioactive pyrano[2,3-b]pyrans (possessing a multi-substituted bicyclic backbone). Copyright
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 and structure-activity relationships of potent new angiotensin converting enzyme inhibitors containing saturated bicyclic amino acids
Blankley,Kaltenbronn,DeJohn,Werner,Bennett,Bobowski,Krolls,Johnson,Pearlman,Hoefle
, p. 992 - 998 (2007/10/02)
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