Synthesis of diastereomerically enriched 2-bromoesters and their reaction with nucleophiles

Chirality

Volumn 13, Issue 2, 2001, Pages 102-108

  Ammazzalorso, Alessandra ^a   Amoroso, Rosa ^a   Bettoni, Giancarlo ^a   De Filippis, Barbara ^a  

^a UNIVERSITY OF CHIETI   (Italy)

Author keywords

(R) pantolactone; 2 substituted carboxylic acids; Dibenzylaminoalchols; Ester derivatives; Nucleophilic displacement

Indexed keywords

2 BROMOACID; 2 BROMOESTER; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; PANTOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0035142546     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/1520-636X(2001)13:2<102::AID-CHIR1005>3.0.CO;2-E     Document Type: Article

References (8)

1. Ferorelli S, Loiodice F, Tortorella V, Amoroso R, Bettoni G, Conte-Camerino D, De Luca A. Isosteres of chiral clofibric acid analogs: synthesis, absolute configuration and HPLC detection of the optical purity. Farmaco 1997;52:367-374.
2. Durst T, Koh K. Asymmetric synthesis of alpha-halo esters. Tetrahedron Lett 1992;33:6799-6802.
3. Amoroso R, Bettoni G, Tricca ML Synthesis of (R)-aryloxy acids by SN2 reaction from diastereomerically enriched α-bromo esters. Synlett 1998;363-364.
4. Amoroso R, Bettoni G, De Filippis B, Tricca ML. Synthesis of 2-aryloxy acids analogues of clofibrate via dynamic kinetic resolution. Chirality 1999;11:483-486.
5. Ward RS, Pelter A, Goubet D, Pritchard M. Diastereoselective synthesis of α-bromoamides leading to diastereomerically enriched α-amino-, α-hydroxy- and α-thiocarboxylic acid derivatives. Tetrahedron: Asymmetry 1995;6:469-498.
6. Koh K, Durst T. Stercoselcctive SN2 reaction of the (R)-pantolactone ester of racemic α-halo carboxylic acids with aryloxides. A synthesis of (S)-2-aryloxy and (S)-2-hydroxy acids. J Org Chem 1994;59:4683-4686.
7. O'Meara J, Gardee N, Jung M, Ben RN, Durst T. Enantioselectivesynthesis of β-dibenzylamino alcohols via a dynamic kinetic resolution of α-halo acids. J Org Chem 1998;63:3117-3119.
8. Reetz MT, Drewes MW, Schmilz A. Stereoselektive synthese von-aminoalkoholen aus optisch aktiven-aminosaeuren. Angew Chem 1987:99:1186-1188.