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000082180 0247_ $$2doi$$a10.1002/chir.20260
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000082180 1001_ $$0P:(DE-HGF)0$$aMeyer, U.$$b0
000082180 1101_ $$aDESY$$bExperiments with synchrotron radiation
000082180 245__ $$aBicyclic glutamic acid derivatives
000082180 260__ $$aNew York, NY [u.a.]$$bWiley Interscience$$c2006
000082180 300__ $$a394
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000082180 440_0 $$0PERI:(DE-600)2001237-8$$aChirality$$v18$$x0899-0042$$y383
000082180 500__ $$3Converted on 2013-05-30 11:35
000082180 500__ $$3Converted on 2013-06-21 19:20
000082180 520__ $$aFor the second-generation asymmetric synthesis of the trans-tris(homoglutamic) acids via Strecker reaction of chiral ketimines, the cyanide addition as the key stereodifferentiating step produces mixtures of diastereomeric alpha-amino nitrile esters the composition of which is independent of the reaction temperature and the type of the solvent, respectively. The subsequent hydrolysis is exclusively achieved with concentrated H(2)SO(4) yielding diastereomeric mixtures of three secondary alpha-amino alpha-carbamoyl-gamma-esters and two diastereomeric cis-fused angular alpha-carbamoyl gamma-lactams as bicyclic glutamic acid derivatives, gained from in situ stereomer differentiating cyclisation of the secondary cis-alpha-amino alpha-carbamoyl-gamma-esters. Separation was achieved by CC. The pure secondary trans-alpha-amino alpha-carbamoyl-gamma-esters cyclise on heating and treatment with concentrated H(2)SO(4), respectively, to diastereomeric cis-fused angular secondary alpha-amino imides. Their hydrogenolysis led to the enantiomeric cis-fused angular primary alpha-amino imides. The configuration of all compounds was completely established by NMR methods, CD-spectra, and by X-ray analyses of the (alphaR,1R,5R)-1-carbamoyl-2-(1-phenylethyl)-2-azabicyclo[3.3.0]octan-3-one and of the trans-alphaS,1S,2R-2-ethoxycarbonylmethyl-1-(1-phenylethylamino)cyclopentanecarboxamide.
000082180 536__ $$0G:(DE-H253)POF1-DORIS-PETRA-20130405$$aFacility (machine) DORIS/PETRA (POF1-DORIS-PETRA-20130405)$$cPOF1-DORIS-PETRA-20130405$$fPOF I$$x0
000082180 588__ $$aDataset connected to Pubmed
000082180 650_7 $$00$$2NLM Chemicals$$aAmino Acids, Cyclic
000082180 650_7 $$00$$2NLM Chemicals$$aEsters
000082180 650_7 $$00$$2NLM Chemicals$$aSolvents
000082180 650_7 $$00$$2NLM Chemicals$$aSulfuric Acids
000082180 650_7 $$056-86-0$$2NLM Chemicals$$aGlutamic Acid
000082180 650_7 $$0O40UQP6WCF$$2NLM Chemicals$$asulfuric acid
000082180 650_2 $$2MeSH$$aAmino Acids, Cyclic: chemistry
000082180 650_2 $$2MeSH$$aAmino Acids, Cyclic: metabolism
000082180 650_2 $$2MeSH$$aCircular Dichroism
000082180 650_2 $$2MeSH$$aCrystallography, X-Ray
000082180 650_2 $$2MeSH$$aCyclization
000082180 650_2 $$2MeSH$$aEsters: chemistry
000082180 650_2 $$2MeSH$$aGlutamic Acid: analogs & derivatives
000082180 650_2 $$2MeSH$$aGlutamic Acid: chemistry
000082180 650_2 $$2MeSH$$aHot Temperature
000082180 650_2 $$2MeSH$$aHydrolysis
000082180 650_2 $$2MeSH$$aModels, Chemical
000082180 650_2 $$2MeSH$$aMolecular Structure
000082180 650_2 $$2MeSH$$aNuclear Magnetic Resonance, Biomolecular
000082180 650_2 $$2MeSH$$aSolvents: chemistry
000082180 650_2 $$2MeSH$$aStereoisomerism
000082180 650_2 $$2MeSH$$aSulfuric Acids: pharmacology
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000082180 7001_ $$0P:(DE-HGF)0$$aBisel, P.$$b1
000082180 7001_ $$0P:(DE-H253)PIP1001249$$aWeckert, E.$$b2
000082180 7001_ $$0P:(DE-HGF)0$$aFrahm, A. W.$$b3
000082180 773__ $$0PERI:(DE-600)2001237-8$$a10.1002/chir.20260$$gVol. 18, p. 394$$p394$$q18<394$$tChirality$$v18$$x0899-0042$$y2007
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000082180 9141_ $$a          Erratum:  Chirality, 2007, 19 (8), 654. (c) Wiley-Liss, Inc. No copyright permission for full text.$$y2007
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