Aluminum Chloride-Mediated Kinetic Resolution of Racemic γ-Substituted-γ-Lactones

Chirality

Volumn 16, Issue 5, 2004, Pages 336-338

  Patil, Sudhir T ^a   Karnik, Anil V ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

substituted lactones; (S) ( ) 1 phenylethylamine; Anhydrous aluminum chloride; Kinetic resolution

Indexed keywords

ALUMINUM CHLORIDE; GAMMA LACTONE DERIVATIVE; PHENETHYLAMINE;

ARTICLE; CHIRALITY; PRIORITY JOURNAL; PURIFICATION; RACEMIZATION; RING OPENING; SUBSTITUTION REACTION;

ALUMINUM COMPOUNDS; AMMONIUM CHLORIDE; CERIUM; CHLORIDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; KINETICS; LACTONES; MODELS, CHEMICAL; OXYGEN; PHENETHYLAMINES; QUATERNARY AMMONIUM COMPOUNDS; STEREOISOMERISM; TEMPERATURE;

EID: 1942540106     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20036     Document Type: Article

References (23)

1. Ohloff G. Recent developments in the field of naturally-occurring aroma components. In: Progress in chemistry of organic natural products, vol. 35. Eien: Springer; 1978.
2. Ohkuma T, Kitamura M, Noyori R. Enantioselective synthesis of 4-substituted γ-lactones. Tetrahedron Lett 1990;31:5509-5512.
3. Ojima I, Kogure T, Kumagai M. Reduction of carbonyl compounds via hydrosilylation. Asymmetric reduction of ketoesters via hydrosilylation, catalysed by rhodium complex with chiral phospine ligands. J Org Chem 1977;42:1671-1679.
4. Gutman AL, Bravdo T. Enzyme-catalysed enantioconvergent lactonisation of γ-hydroxy diesters in organic solvents. J Org Chem 1989; 54:4263-4265.
5. Vijay N, Jaya P, Tesmol G. A facile synthesis of optically active lactones using benzyl-3,6,-anhydro glucofuranoside as chiral auxillary. Tetrahedron 1997;53,44:15061-15068.
6. Pollet P, Gelin S. Tetronic acids and derivatives-IV' synthesis and lactonisation of γ-acetoxy β-keto esters. Tetrahedron 1978;34: 1453-1455.
7. Ben RN, Durst T. Synthesis of optically active α-amino esters via dynamic kinetic resolution: a mechanistic study. J Org Chem 1999; 64:7700-7706.
8. Francotte E, Lohamann D. Analytical and preparative resolution of racemic γ- and δ-lactone by chromatography on cellulose triacetate. Relationship between elution order and absolute configuration. Helv Chem Acta 1987;70:1569-1582.
9. Castells CB, Carr PW. Cellulose tris (3,5,-dimethyl phenyl carbamate) coated zirconia as a chiral stationary phase for HPLC. Anal Chem 1999;71:3013-3021.
10. Kim I, Okamoto Y, Carr PW, Ryu J, Park JH. Amylose tris (3,5-dimethyl phenyl carbamate) coated zirconia as a chiral stationary phase for micro HPLC. Bull Kor Chem Soc 2002;23:1014-1016.
11. Ekborg-Ott K, Liu Y, Armstrong DW. Highly enantioselective HPLC separation using covantly bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase. Chirality 1998;10:434-438.
12. Yonggang C, Mcdaid P, Deng L. Asymmetric alcoholysis of cyclic anhydrides. Chem Rev 2003;103:2965-2983.
13. Cheng Y, Deng L. Parallel kinetic resolution of monosubstituted succinic anhydrides catalyzed by a modified chinchona alkaloids. J Am Chem Soc 2001;123:1302-11303.
14. Hang J, Tians K, Tang L, Deng L. Asymmetric synthesis of α-amino acids via chincona alkaloid-catalyzed by kinetic resolution of urethane-protected α-amino acid,N-carboxy anhydride. J Am Chem Soc 2001; 123:12696-12697.
15. Johnson CD, Lane S, Edwards PN, Taylor PJ. Prodrugs based on masked lactones, cyclisation of γ-hydroxy amides. J Org Chem 1988; 53:5130-5139.
16. Strekowsi L, Visnick M, Battiste MA. Resolution and assignment of absolute configuration to the enantiomers of anastrephin and epianastrephin and their analogues. J Org Chem 1986;51:4836-4839.
17. Helmchen G, Nill G. Preparative scale directed resolution of enantiomeric amines via liquid chromatography of diastereomeric 4-hydroxybutyramides. Angew Chem Int Ed 1979;18:65-66.
18. Kumazawa T, Harakawa H, Obase H, Oiji Y, Tanka H, Shuto K, Ishii A, Nakamiz N, Oka T. Synthesis and antiulcer activity of 5,11-dihydro benzoxepino(3,4-b) pyridines. J Med Chem 1988;31:779-785.
19. Lesimple P, Bigg DCH. Aluminum chloride mediated aminolysis of lactones: a general method for the preparation of co-hydroxyalkylamides. Synthesis 1991;306.
20. Nagarajan A, Porchezhiyan V, Balsubrramanian T, Ramanujam S. Synthesis of γ-phenyl-γ-butyrolactone. Ind J Chem 1985;24B: 1202-1203.
21. Inove T, Kiyota H, Oritani T. Synthsis of both enantiomer of cis-α-irone and cis-γ-irone, principle constituents of iris oil, via resolution of (±)-2,2,4,trimethyl-3-cyclohexene-1-carboxylic acid. Tetrahedron Asymmetry 2001;11:3807-3818.
22. Pascal De T, Apostolos F, Bernard P. First preparative enantiomer resolution of prilindole a potent antidepressant drug. Helv Chem Acta 1998;81:539-547.
23. 3).