Stereocontrolled synthesis of (-)-kainic acid from trans-4-hydroxy-L- proline

Journal of Organic Chemistry

Volumn 70, Issue 26, 2005, Pages 10860-10863

  Poisson, Jean François ^a   Orellana, Arturo ^a   Greene, Andrew E ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; COPPER COMPOUNDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CUPRATES; DIASTEREOSELECTIVE ENOLATE; KAINIC ACID;

ORGANIC ACIDS;

CARBOXYLIC ACID DERIVATIVE; HYDROXYPROLINE; KAINIC ACID; KETONE; PYRROLIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 29944432210     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051508t     Document Type: Article

References (57)

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53. The following yields and disatereoselectivities were obtained: benzyl bromoacetate (92%, 14:1), tert-butyl bromoacetate (83%, 16:1), methyl iodide (66%, 8:1), allyl iodide (80%, 14:1).
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55. max range 3.22-74.89°, 5344 measured reflections, 4438 [R(int) = 0.03897] independent reflections, R(1) [1 > 2σ(I)] = 0.0652, wR2 [all data] = 0.0924, GoF (all data) = 1.962. The crystallographic information file (CIF) has been deposited at the Cambridge Crystallographic Data Centre as CCDC 276163. These data can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CBZ 1EZ, UK.; fax (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk.
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