Enantioselective synthesis of (R)-2-methylalkanoic acids: A convenient approach to α-substituted chiral carboxylic acid derivatives

Synthetic Communications

Volumn 34, Issue 18, 2004, Pages 3435-3441

  Shirali, Shyam ^a   Zhang, Aijun ^a  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

Alkylation; Chiral; Enantioselctive; Lithium hydroperoxide

Indexed keywords

ALKANOIC ACID; CARBOXYLIC ACID DERIVATIVE; IMIDAZOLINE DERIVATIVE; LITHIUM;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DEACYLATION; ENANTIOSELECTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 5444255859     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200030650     Document Type: Article

References (24)

1. (a) Norin, T. Synthetic and chemical studies on pheromones of some forest pest insects. Pure & Appl. Chem. 1989, 67, 547-550 (and references cited therein);
2. (b) Foye, W.O. Nonstereoidal antiinflammatory drugs. In Principles of Medicinal Chemistry; Lea & Febiger: London, 1989; 503-530.
3. (a) Evans, D.A. Stereoselective alkylation reaction of chiral metal enolates. In Asymmetric Synthesis; Morrison, J.D., Ed.; Academic Press: New York, 1984; Vol. 3, 1-110;
4. (b) Meyer, A.I. Asymmetric carbon-carbon bond formation from chiral oxazolines. Acc. Chem. Res. 1978, 11, 375-381.
5. Evans, D.A.; Britton, T.C.; Ellman, J.A. Constrasteric carboximide hydrolysis with lithium hydroperoxide. Tetrahedron Lett. 1987, 28 (49), 6141-6144.
6. Koll, P.; Lutzen, A. Resolution of racemic carboxylic and sulfonic acids via D-Xylose derived new cyclo carbamate reagents (oxazolidin-2-ones). Tetrahedron: Asymmetry 1995, 6 (1), 43-46.
7. (a) Negrete, G.R.; Konopelski, J.P. Asymmetric alkylations of N-acyl dihydropyrimidinones. Tetrahedron: Asymmetry 1991, 2, 105-108;
8. (b) Guillena, G.; Najera, C. PTC and organic based-LiCl assisted alkylation of imidazolidinone-glycine iminic derivatives for the asymmetric synthesis of α-amino acids. Terahedron: Asymmetry 1998, 9, 3935-3938;
9. (c) Guillena, G.; Najera, C. (4R,5R)-Dimethyl-4-phenylimidazolidin-2-one as a chiral auxiliary for the diastereoselective alkylation of a new iminic glycine derivative: practical asymmetric synthesis of α-amino acids. Terahedron: Asymmetry 1998, 9, 1125-1129;
10. (d) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Microwave-assisted ring expansion of N-acetyl 3′-unsubstituted aziridine in the presence of Lewis acids. Tetrahedron: Assymmetry 2001, 57, 2807-2812;
11. (e) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Ring expansion of N-acyl aziridine-2-imides to oxazoline-4-imides, useful precursors of pure β-hydroxy α-aminoacids. Tetrahedron Lett. 1997, 38 (39), 6953-6956;
12. (f) Guillena, G.; Najera, C. 1,5-Dimethyl-4-phenylimidazolidin-2-one- derived iminic glycinimides: Useful new reagents for practical asymmetric synthesis of α-amino acids. J. Org. Chem. 2000, 65, 7310-7322.
13. (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. Diastereoselective alkylation of 3-acylimidazolidin-2-ones: Synthesis of (R)- and (S)-lavandulol. J. Org. Chem. 1988, 53, 2354-2356;
14. (b) Cardillo, G.; Orena, M.; Romero, M.; Sandri, S. Enantioselective synthesis of 2-benzyloxy alcohols and 1,2-diols via alkylation of chiral glycolate imides. A convenient approach to optically active glycerol derivatives. Tetrahedron 1989, 45 (5), 1501-1508;
15. (c) Nishi, T.; Sakurai, M.; Sato, S.; Kataoka, M.; Morisawa, Y. Asymmetric synthesis of 2-substituted-3-aminocarbonyl propionic acid. Chem. Pharm. Bull. 1989, 37 (8), 2200-2203;
16. (d) Bradbury, R.H.; Revitt, J.M.; Revitt, J.E.; Waterson, D. An efficient synthesis of the γ-lactone corresponding to a hydroxyethylene dipeptide isostere using stereoselective bromolactonisation of a chiral acyloxazolidinone. Tetrahedron Lett. 1989, 30 (29), 3845-3848;
17. (e) Harre M.; Trabandt, J.; Westermann, J. Convenient preparation of dimethyl [93S0-3-methyl-2-oxo-5-octynyl]-phosphonate. Leibigs Ann. Chem. 1989, 1081-1083;
18. (f) Seebach, D.; Dziadulewicz, E.; Behrendt, L.; Cantoreggi, S.; Fitzi, R. Synthesis of nonproteinogenic (R)- or (S)-amino acids. Analogues of phenylalanine, isotopically labelled and cyclic amino acids from tert-butyl 2-(tert-butyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate (Boc-BMI). Liebigs Ann. Chem. 1989, 1215-1232.
19. Close, W.J. The conformation of the ephedrines. J. Org. Chem. 1950, 15, 1131-1134.
20. Still, W.C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2924.
21. (a) Kashiwagi, T.; Kozuka, S.; Oae, S. The decomposition of diacyl peroxides-I The thermal decomposition of primary and secondary diacyl peroxide. Tetrahedron 1970, 26 (15), 3619-3629;
22. (b) Harrington-Frost, N.; Leuser, H.; Calaza, M.; Krieisel, F.; Knochel, P. Highly stereoselective anti SN2? substitutions of (Z)-allylic pentafluorobenzoates with polyfunctionalized zinc-copper reagents. Org. Lett. 2003, 5 (12), 2111-2114;
23. (c) Nakazaki, M.; Maeda, M. Medium ring-size effect in 2′,3-polymethylen-3-alkyl-2-phenylindolenines. Bull. Chem. Soc. Jpn 1961, 53 (8), 1380-1387;
24. (d) Staudinger, M.; Ruzika, L. Investigation to cyclopentanolonderivative and their comparison with the pyrethrolon. Hel. Chim. Acta 1924, 7, 377-390.