100243-39-8Relevant articles and documents
Further evidence on the PET cyclization of α-silylmethylamines tethered with non-activated olefins: Demonstration by the total synthesis of (-)-retronecanol
Pandey, Ganesh,Chakrabarti, Debasish
, p. 2285 - 2288 (1996)
The total synthesis of (-)-retronecanol, in order to provide convincing evidence for the PET cyclization of α-trimethylsilylmethyl amines with tethered non-activated olefins, is reported.
Enantioselective addition of diethylzinc to aromatic aldehydes catalysed by chiral ligands derived from L-hydroxyproline
Mehler,Martens,Wallbaum
, p. 2691 - 2699 (1993)
The lithium salts of chiral auxiliaries 2-4 derived from L-hydroxyprolin (2S,4R)-1 catalysed the enantioselecive addition of diethylzinc to aromatic aldehydes to afford sec alcohols in up to 80% optical purity.
Synthesis of (3R)-carboxy pyrrolidine (a β-proline analogue) and its oligomer
Kim, Yong Jip,Kaiser, Donald A.,Pollard, Thomas D.,Ichikawa, Yoshitaka
, p. 2417 - 2419 (2000)
A decamer of a β-amino acid analogue of L-proline, (3R)-carboxy pyrrolidine (β-proline), was synthesized from a readily available (R)-glycidol. It was found to possess a rigid secondary structure, as evidenced by its CD spectrum. The β-proline decamer, however, failed to bind to profilin, whereas the corresponding α-L-proline decamer bound tightly to this protein. (C) 2000 Published by Elsevier Science Ltd.
A NOVEL DECARBOXYLATION OF α-AMINO ACIDS. A FACILE METHOD OF DECARBOXYLATION BY THE USE OF 2-CYCLOHEXEN-1-ONE AS A CATALYST
Hashimoto, Mitsunori,Eda, Yutaka,Osanai, Yasutomo,Iwai, Toshiaki,Aoki, Seiichi
, p. 893 - 896 (1986)
In the presence of a catalytic amount of 2-cyclohexen-1-one, decarboxylation of α-amino acids proceeds smoothly and affords the corresponding amino compounds in good yields.Optically active amino compounds, (3R)-(-)-3-hydroxypyrrolidine and (2R)-(-)-2-hydroxypropylamine are obtained in 93percent and 80percent yields, respectively.
Constrained β-alanine based GpIIb/IIIa antagonists
Klein, Scott I.,Czekaj, Mark,Molino, Bruce F.,Valeria, Chu
, p. 1773 - 1778 (1997)
The concepts of centrally constrained and peptide based fibrinogen receptor antagonists have been successfully combined into a single series of analogs which have been demonstrated to be potent inhibitors of platelet aggregation.
Enzymatic ammonolysis of ethyl (±)-4-chloro-3-hydroxybutanoate. Chemoenzymatic syntheses of both enantiomers of pyrrolidin-3-ol and 5- (chloromethyl)-1,3-oxazolidin-2-one
Garcia-Urdiales, Eduardo,Rebolledo, Francisca,Gotor, Vicente
, p. 721 - 726 (1999)
Lipase B from Candida antarctica efficiently catalysed the kinetic resolution of ethyl (±)-4-chloro-3-hydroxybutanoate through an ammonolysis reaction. Using this methodology, both enantiomers of 4-chloro-3- hydroxybutanamide were prepared and converted into pyrrolidin-3-ol and 5- (chloromethyl)-1,3-oxazolidin-2-one by simple processes consisting of a reduction reaction and a Hofmann rearrangement, respectively.
Decarboxylation of α-amino acids containing two and three stereogenic centers: A simple one-step procedure to prepare two optically active β- amino alcohols and a bicyclic pyrrolidine derivative
Wallbaum,Mehler,Martens
, p. 1381 - 1387 (1994)
The decarboxylation of L-threonine (2S,3R)-1, L-hydroxyproline (2S,4R)-2 and D-2-azabicyclo[3.3.0]octan-3-carboxylic acid (1R,3R,5R)-5 yield in a simple one-step procedure the corresponding optically active β-amino alcohols (R)-3 and (R)-4 and the bicyclic pyrrolidine derivative (1R,5R)-6 in 72-82% yield and >99% ee.
Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of nucleobases
Ko?alka, Petr,Pohl, Radek,Rejman, Dominik,Rosenberg, Ivan
, p. 5763 - 5774 (2006)
The synthesis of novel 3-pyrrolidinyl derivatives of nucleobases is described. Starting from malic acid, we improved the synthesis of both racemic and optically active N-benzyl-3-hydroxypyrrolidine-2,5-diones, which were transformed in four steps into N-tert-butyloxycarbonyl-3-mesyloxypyrrolidines, the key synthons for the alkylation of purine and pyrimidine nucleobases. Alkylations of cesium salts of purines and sodium salts of pyrimidines with N-tert-butyloxycarbonyl-3-mesyloxypyrrolidines proceeded smoothly, giving high yields of 9-substituted purine derivatives and moderate yields of 1-substituted pyrimidine derivatives. Using (S)-N-tert-butyloxycarbonyl-3-mesyloxypyrrolidine as the same intermediate for the synthesis of both enantiomeric N-Boc-3-pyrrolidinyladenines, and considering the results obtained on chiral HPLC analysis of the products, we proved that nucleophilic displacement of the mesyloxy group proceeded with inversion and not with retention of the configuration. Prepared compounds were tested for cytostatic and antiviral properties, but no significant activity was found.
Synthesis method of (R)-3-hydroxypyrrolidine
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Paragraph 0021-0026, (2021/04/17)
The invention relates to the technical field of organic synthesis, in particular to a synthesis method of (R)-3-hydroxy pyrrolidine, which comprises the following steps: reacting Lhydroxyproline in a reaction medium at 80-160 DEG C under the action of a decarboxylation catalyst, and carrying out reduced pressure distillation after the reaction is completed, thereby obtaining the (R)-3-hydroxy pyrrolidine, and the carboxylic acid decarboxylation catalyst is selected from methyl isobutyl or cyclohexanone. The (R)-3-hydroxy pyrrolidine synthesis method provided by the invention uses the cheap, safe and non-toxic decarboxylation catalyst and the reaction medium which is easier to recover, achieves higher yield than the prior art, and is suitable for industrial large-scale production.
Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family
Afanasyev, Oleg I.,Podyacheva, Evgeniya,Rudenko, Alexander,Tsygankov, Alexey A.,Makarova, Maria,Chusov, Denis
, p. 9347 - 9360 (2020/08/14)
A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.
