Racematspaltungen mit Substanzfamilien

Vries, Ton R.; Wynberg, Hans; Echten, Erik van; Koek, J. H.; Hoeve, Wolter ten; Kellogg, Richard M.; Broxterman, Quirinus B.; Minnaard, Adriaan J.; Kaptein, Bernard; Sluis, S. Van Der; Hulshof, L.A.; Kooistra, Jaap

doi:10.1002/(sici)1521-3757(19980904)110:17<2491::aid-ange2491>3.0.co;2-x

Cited by 56 publications

(37 citation statements)

References 13 publications

(7 reference statements)

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“…After the Leuckart reductive amination of the corresponding bis-aldehydes, the reaction mixture contained a rac:-meso ratio of 85:15 and 80:20, respectively, according to 1 H NMR analysis. After bulb-to-bulb distillation, the only products isolated were racemic 42 and 43 (rac:meso > 99:1).…”

Section: -Propylbutylaminementioning

confidence: 99%

“…After Kugelrohr distillation, the only product isolated was racemic 42 (rac:meso > 99:1) as a colourless oil, 53 % yield after bulb-to-bulb distillation; 1 Bifunctional additives (R,R)-44 and (R,R)-45 were synthesised as enantiopure compounds by using a three-step procedure reported previously. [5] Procedure for the synthesis of (R)-phenylglycine amide (PGA)-diimines:…”

Section: -Propylbutylaminementioning

confidence: 99%

“…[1,2] As first described an equimolar mixture of, in general, three resolving agents of the same family (i.e., with close structural analogy, common absolute stereochemistry) was used. Non-stoichiometric incorporation of resolving agents and often improved diastereomeric excesses of the first salts were observed.…”

Section: Introductionmentioning

confidence: 99%

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The Dutch Resolution Variant of the Classical Resolution of Racemates by Formation of Diastereomeric Salts: Family Behaviour in Nucleation Inhibition

Dalmolen

Tiemersma‐Wegman

Nieuwenhuijzen³

et al. 2005

Chemistry A European J

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Section: -Propylbutylaminementioning

confidence: 99%

Section: -Propylbutylaminementioning

confidence: 99%

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The Dutch Resolution Variant of the Classical Resolution of Racemates by Formation of Diastereomeric Salts: Family Behaviour in Nucleation Inhibition

Dalmolen

Tiemersma‐Wegman

Nieuwenhuijzen³

et al. 2005

Chemistry A European J

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“…An example of such a process in which two or more molecules are involved is the resolution of racemates by the Dutch resolution methodology. [5] Here, potential resolving agents are exposed to a racemate in a cocktail fashion. Solid solutions may have a higher density and a lower solubility than pure components.…”

Section: Introductionmentioning

confidence: 61%

Molecular Selectivity and Cooperativity in the Clathrate-Type Complexation of Cephradine

Kemperman¹,

Gelder

Dommerholt³

et al. 2002

Eur. J. Org. Chem.

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“…[7,8b] In this paper we report the preparation of easily accessible substituted 1-aryl-1-butylamines and 1-aryl-3-butenylamines, which we intend to use as new families of resolving agents in ''Dutch Resolution experiments''. [11] A metal-mediated Cope reaction ( Figure 1) is a key element of the synthesis. There is extensive precedent for such reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Enantiopure 1‐Aryl‐1‐butylamines and 1‐Aryl‐3‐butenylamines by Diastereoselective Addition of Allylzinc Bromide to Imines Derived from (R)‐Phenylglycine Amide.

et al. 2004

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Synthesis of enantiopure 1-aryl-1-butylamines and 1-aryl-3-butenylamines by diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide Dalmolen, Jan; Sluis, Marcel van der; Nieuwenhuijzen, José W.; Meetsma, Auke; Lange, Ben de; Kaptein, Bernard; Kellogg, Richard M.; Broxterman, Quirinus B. Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Keywords: Allylation / Asymmetric synthesis / Chiral auxiliaries / DiastereoselectivityThe synthesis of enantiopure 1-aryl-1-butylamines via a highly diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide is reported. These are synthesised by a three-step procedure, which involves: (a) formation of the chiral imines; (b) asymmetric addition of the allylzinc reagent; (c) removal of the chiral auxiliary by IntroductionEnantiomerically pure amines with a chiral centre at the α-position are valuable synthons in the synthesis of biologically active natural products and compounds of pharmaceutical interest.[1] One of the strategies used to obtain chiral amines is an asymmetric 1,2-addition of nucleophiles to the electrophilic CϭN imino group of chiral aldimines (Scheme 1). Other methods include e.g. catalytic asymmetric addition of dialkylzinc to imines, [2] diastereoselective reduction of chiral imines, [3] enantioselective reduction of prochiral imines [4] and oximes, [5] or use of a transaminase. [6] Scheme 1. Synthesis of enantiomerically enriched primary amines by asymmetric 1,2-addition Enantiomerically pure imines can be generated, in most cases fairly easily, by condensation of an enantiopure amine R 2 ϪNH 2 used as a (readily available) chiral auxiliary, with the corresponding carbonyl compound. High asymmetric [a] University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands [b] Syncom B.V., Kadijk 3, 9747 AT Groningen, The Netherlands E-mail: R.M.Kellogg@syncom.nl [c] means of a reductive or non-reductive method. The reductive method provides 1-aryl-1-butylamines whereas the non-reductive method preserves the double bond to afford 1-aryl-3-butenylamines.( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004) induction during the addition can be achieved by using imines derived from chiral auxiliaries such as α-arylethylamines, [7] β-amino alcohols, β-alkoxy amines, and α-amino acid esters. [8] A common feature of the latter three auxiliaries is the presence of a second heteroatom, which is capable of rigidifying the transition state of the 1,2-addition through chelation. [7] This effect is also referred to as ''chelation control''. [9] Drawbacks are the availability, in some cases, of only one enantiomer, high costs, low re...

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Racematspaltungen mit Substanzfamilien

Cited by 56 publications

References 13 publications

The Dutch Resolution Variant of the Classical Resolution of Racemates by Formation of Diastereomeric Salts: Family Behaviour in Nucleation Inhibition

The Dutch Resolution Variant of the Classical Resolution of Racemates by Formation of Diastereomeric Salts: Family Behaviour in Nucleation Inhibition

Molecular Selectivity and Cooperativity in the Clathrate-Type Complexation of Cephradine

Synthesis of Enantiopure 1‐Aryl‐1‐butylamines and 1‐Aryl‐3‐butenylamines by Diastereoselective Addition of Allylzinc Bromide to Imines Derived from (R)‐Phenylglycine Amide.

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