(R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries for the asymmetric synthesis of α-hydroxy acids

Tetrahedron Asymmetry

Volumn 8, Issue 11, 1997, Pages 1877-1894

  Camps, Pelayo ^a   Pérez, Francesc ^a   Soldevilla, Núria ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; HYDROXYACID;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; HYDROLYSIS; PRIORITY JOURNAL;

EID: 0343683426     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00176-6     Document Type: Article

References (22)

1. Camps, P.; Giménez, S.; Font-Bardia, M.; Solans, X. Tetrahedron: Asymmetry, 1995, 6, 985-990.;
2. Camps, P.; Giménez, S. Tetrahedron: Asymmetry, 1995, 6, 991-1000.
3. Camps, P.; Giménez, S. Tetrahedron: Asymmetry, 1996, 7, 1227-1234.
4. Durst, T.; Koh, K.; Tetrahedron Lett., 1992, 33, 6799-6802.
5. Koh, K.; Durst, T.; J. Org. Chem., 1994, 59, 4683-4686.
6. Ward, R. S.; Pelter, A.; Goubet, D.; Pritchard, M. C.; Tetrahedron: Asymmetry, 1995, 6, 93-96.
7. Ward, R. S.; Pelter, A.; Goubet, D.; Pritchard, M. C.; Tetrahedron: Asymmetry, 1995, 6, 469-498.
8. Kubo, A.; Takahashi, M.; Kubota, H.; Nunami, K.; Tetrahedron Lett., 1995, 36, 6251-6252.
9. Kubota, H.; Kubo, A.; Takahashi, M.; Shimizu, R.; Da-te, T.; Okamura, K.; Nunami, K.; J. Org. Chem., 1995, 60, 6776-6784.
10. Watabe, K.; Chang, S. -C.; Gil-Av, E.; Koppenhoefer, B.; Synthesis, 1987, 225-228.
11. Saito, K.; Harada, K.; Bull. Chem. Soc. Japan, 1989, 62, 2562-2566.
12. For some enantioselective reduction of (α-keto esters to α-hydroxy esters, see: a) Singh, V. K.; Synthesis, 1992, 605-617.
13. b) Hapiot, F.; Agbossou, F.; Morteux, A.; Tetrahedron: Asymmetry, 1995, 6, 11-14.
14. For some diastereoselective reduction of α-keto esters derived from enantiopure alcohols, to the corresponding α-hydroxy esters, see: a) Akiyama, T.; Nishimoto, H.; Ozaki, S.; Tetrahedron Lett. 1991, 32, 1335-1338.
15. b) Xiang, Y. B.; Snow, K.; Belley, M.; J. Org. Chem., 1993, 55, 993-994.
16. For another enantioselective approach to α-hydroxy acids, see: Evans, D. A.; Morrissey, M. M.; Dorow, R. L.; J. Am. Chem. Soc., 1985, 107, 4346-4348.
17. Corey, E. J.; Link, J. O.; Tetrahedron Lett., 1992, 33, 3431-3434.
18. For reviews on dynamic kinetic resolution see: a) Noyori, R.; Tokunaga, M.; Kitamura, M.; Bull. Chem. Soc. Jpn., 1995, 68, 36-56.
19. b) Ward, R. S.; Tetrahedron: Asymmetry, 1995, 6, 1475-1490.
20. For a related case of dynamic kinetic resolution see: Matteson, D. S.; Man, H. W.; J. Org. Chem., 1994, 59, 5734-5741.
21. th ed., The Chemical Rubber Publishing Co., Boca Raton, Florida, 1988-89.
22. Aldrich, Catálogo de Química Fina, 1996-97, Aldrich Chemical Co., Sigma-Aldrich Química, S.A., Spain.