Journal ArticleDOI
Synthetic application of chiral pool derived heterocycles
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This article is published in Journal of Heterocyclic Chemistry.The article was published on 2000-05-01. It has received 22 citations till now.read more
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Zinc(II) perchlorate hexahydrate catalyzed opening of epoxide ring by amines: applications to synthesis of (RS)/(R)-propranolols and (RS)/(R)/(S)-naftopidils.
TL;DR: Zinc(II) perchlorate hexahydrate was found to be the best catalyst compared to other metal perchlorates and the applicability of the methodology was demonstrated by the synthesis of cardiovascular drugs propranolol and naftopidil as racemates and optically active enantiomers.
Journal ArticleDOI
Scope and limitations of montmorillonite K 10 catalysed opening of epoxide rings by amines
TL;DR: In this paper, aniline reacts selectively at the less hindered carbon of other unsymmetrical epoxides, which is controlled by the electronic and steric factors associated with the epoxide and the amine.
Journal ArticleDOI
Zinc tetrafluoroborate hydrate as a mild catalyst for epoxide ring opening with amines: scope and limitations of metal tetrafluoroborates and applications in the synthesis of antihypertensive drugs (RS)/(R)/(S)-metoprolols.
TL;DR: The role of the metal tetrafluoroborates is envisaged as "electrophile nucleophile dual activation" through cooperativity of coordination, charge-charge interaction, and hydrogen-bond formation that rationalizes the catalytic efficiency, substrate reactivity, and regioselectivity.
Journal ArticleDOI
Sulfamic acid as an efficient and recyclable catalyst for the ring opening of epoxides with amines and anilines: An easy synthesis of β-amino alcohols under solvent-free conditions
TL;DR: In this paper, the application of sulfamic acid as an efficient and green catalyst for the ring opening of epoxides by aliphatic and aromatic amines under solvent-free conditions is described.
Journal ArticleDOI
Ring opening of epoxides catalysed by poly(amidoamine) dendrimer supported on crosslinked polystyrene
TL;DR: In this paper, three generations of polystyrene supported poly(amidoamine) dendrimer were synthesized and characterized, and they were found to be efficient organocatalysts in the nucleophilic ring opening of epoxides by anilines.
References
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Journal ArticleDOI
Über Aminosäuren und Peptide, VIII. Asymmetrische Synthese aromatischer α‐Aminosäuren und N‐Methyl‐α‐aminosäuren. — Synthese von L‐Dopa. — Über die katalytische Hydrierung ungesättigter Cyclodipeptide
Hans Poisel,Ulrich Schmidt +1 more
TL;DR: In this article, the authors investigated the relationship between structure and stereospecifity of alkylidene derivatives of glycyl-L-proline anhydride such as 13b or c and found that no asymmetric induction was observed.
Journal ArticleDOI
Synthesis of asymmetric 1-amino-2-phenylcyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized homochiral olefines
TL;DR: In this paper, homochiral benzylidenediketopiperazine and α-benzoylaminocinnamic esters react with diazomethane giving high diastereomeric ratios of spiropyrazoline derivatives which, on photolysis and acid hydrolysis, gave, respectively, (+)- and (−)-1-amino-2-phenylcyclopropanecarboxylic acids.
Journal ArticleDOI
Asymmetric syntheses of 1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines
Carmen Alcaraz,Ma Dolores Fernández,Ma Pilar de Frutos,Joseé L. Marco,Manuel Bernabé,Concepción Foces-Foces,Felix H. Cano +6 more
TL;DR: In this paper, the structure of all compounds has been assessed by NMR studies and y X-ray crystallography and analysis of an intermediate spiroderivative, and the enantiomerically pure dipeptide of the (1R, 2R) enantiomers with S-proline was also obtained by selective cleavage of the diketopiperazine moiety.
Journal ArticleDOI
Enantioselective synthesis of (+)-(1R,2S)-allocoronamic acid
TL;DR: In this paper, an asymmetric synthesis of (+)-(1R, 2S)-allocoronamic acid was reported, where Diazomethane addition to (Z)-N-( tert -butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride, easily prepared from 2-phenyl-4-propylidene-5(4H)-oxazolone and L-proline, gave in high diastereomeric excess the corresponding spiropyrazoline, which was transformed, on photo
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