118396-01-3Relevant articles and documents
Base-Catalysed Epimerization Behavior and Unusual Reactivity of N-Substituted Derivatives of 2,5-Dicarbalkoxypyrrolidine. Preparation of a Novel Mixed Carbamic Carbonic Anhydride by a 4-(Dimethylamino)pyridine-Catalyzed Acylation
Kemp, D.S.,Curran, Timothy P.
, p. 5729 - 5731 (1988)
The equilibration of cis-trans isomers of 1-substituted 2,5-dicarbalkoxypyrrolidine derivatives (1 = CH2Ph, H, CN, CO2R) results in nearly 1:1 mixtures, contrary to a literature report for 1-benzyl-2,5-dicarbalkoxypyrrolidine.Apparent conversion to the tr
A mechanochemical approach to access the proline-proline diketopiperazine framework
Pétry, Nicolas,Benakki, Hafid,Clot, Eric,Retailleau, Pascal,Guenoun, Farhate,Asserar, Fatima,Sekkat, Chakib,Métro, Thomas-Xavier,Martinez, Jean,Lamaty, Frédéric
, p. 2169 - 2178 (2017/11/16)
Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline-proline dipeptides under solvent-free conditions. A deprotection-cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro-Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.
Switching and Conformational Fixation of Amides Through Proximate Positive Charges
Bartuschat, Amelie L.,Wicht, Karina,Heinrich, Markus R.
, p. 10294 - 10298 (2015/09/01)
Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization. Taking charge of conformation: Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization.
Enantioselective biotransformations of racemic and meso pyrrolidine-2,5-dicarboxamides and their application in organic synthesis
Chen, Peng,Gao, Ming,Wang, De-Xian,Zhao, Liang,Wang, Mei-Xiang
, p. 4063 - 4072 (2012/06/18)
In this paper, we report the amidase-catalyzed hydrolysis of pyrrolidine-2,5-dicarboxamides and their application in organic synthesis. Catalyzed by Rhodococcus erythropolis AJ270, an amidase containing microbial whole cell catalyst, racemic trans-pyrrolidine-2,5-carboxamide was kinetically resolved into (2S,5S)-pyrrolidine-2,5-dicarboxamide and (2R,5R)-5- carbamoylpyrrolidine-2-carboxylic acid in high yields and excellent enantioselectivity. Biocatalytic desymmetrization of meso cis- pyrrolidinedicarboxamide afforded enantiomerically pure (2R,5S)-5- carbamoylpyrrolidine-2-carboxylic acid in an almost quantitative yield. In both kinetic resolution and desymmetrization, the amidase always exhibited excellent 2R-enantioselectivity, although its catalytic efficiency was influenced dramatically by the steric effect of the substituent on the nitrogen atom of pyrrolidine ring. The synthetic potential of biotransformation was demonstrated by the scalable preparation of (2R,5R)- and (2R,5S)-5-carbamoylpyrrolidine-2- carboxylic acids and their conversions to aza-nucleoside analogues and druglike pyrroline-fused diazepin-11(5H)-one compounds.
Synthesis of both enantiomers of C2 symmetric trans-2,5- bis(hydroxymethyl)pyrrolidine. Lipase mediated sequential kinetic resolutions
Sibi,Lu
, p. 4915 - 4918 (2007/10/02)
Lipase mediated sequential kinetic resolution has been employed to give both enantiomers of trans-2,5-bis(hydroxymethyl)pyrrolidine in optically pure form. The effect of different parameters on the ee and yields in these resolutions are also reported.
Studies of N-Terminal Templates for α-Helix Formation. Synthesis and Conformational Analysis of (2S,5S,8S,11S)-1-Acetyl-1,4-diaza-3-keto-5-carboxy-10-thiatricyclo4,8>tridecane (Ac-Hel1-OH)
Kemp, D. S.,Curran, Timothy P.,Davis, William M.,Boyd, James G.,Muendel, Christopher
, p. 6672 - 6682 (2007/10/02)
A convergent synthesis of the title compound, a conformationally restricted analogue of acetyl-L-prolyl-L-proline, from 1-acetyl-2(S)-carboxy-4(S)-mercaptopyrrolidine and trans-1-(tert-butoxycarbonyl)-2(S)-(methoxycarbonyl)-5(S)-pyrrolidine (Ac-Hel1-OH) is reported, along with a synthesis of (2S,8S,11S)-1-acetyl-1,4-diaza-3-keto-10-thiatricyclo4,8>tridecane.In the crystal and in CDCl3 solution the conformation of Ac-Hel1-OH is shown to approximate a staggered orientation at the 8,9-CC bond and an s-cis orientation at the acetyl amide bond.In DMF, DMSO, MeCN, and D2O significant amounts of the s-trans conformer are also present.
Amino Acids, 14. - Diastereoselective Addition of Benzenesulfenyl Chloride to 1-Acryloylproline Esters
Effenberger, Franz,Isak, Heinz
, p. 545 - 552 (2007/10/02)
(S)-Proline esters (S)-1 react with acryloyl chloride (2) to give 1-acryloylproline esters (S)-3 in good yields.Addition of benzenesulfenyl chloride (6) to (S)-3 at -95 deg C in dichloromethane results in 1-proline esters
