Nucleophilic additions of chiral non-racemic enolates to N-benzyl-C-(alkoxymethyl) nitrones

Arkivoc

Volumn 2004, Issue 4, 2004, Pages 48-58

  Merino, Pedro ^a   Franco, Santiago ^a   Mates, Juan A ^a   Merchan, Francisco L ^a   Romero, Pilar ^a   Tejero, Tomas ^a   Uriel, Santiago ^a   Matute, Rosa ^b  

^a CSIC   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Enolates; Hydroxylamines; Isoxazolidines; Nitrones

Indexed keywords

2 BENZYL 3 (BENZYLOXYMETHYL)ISOXAZOLIDIN 5 ONE; 2 BENZYL 3 [(TERT BUTYLDIMETHYLSILOXY)METHYL]ISOXAZOLIDIN 5 ONE; 5 ISOXAZOLIDINONE DERIVATIVE; ACETIC ACID DERIVATIVE; BORNYL ACETATE; HYDROXYLAMINE; ISOXAZOLIDINE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM ENOLATE; MENTHYL ACETATE; N BENZYL C (BENZYLOXYMETHYL)NITRONE; N BENZYL C (TERT BUTYLDIPHENYLSILOXYMETHYL)NITRONE; NITRONE DERIVATIVE; ORGANOMETALLIC COMPOUND; SODIUM DERIVATIVE; SODIUM ENOLATE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; NUCLEOPHILIC ADDITION; RACEMIC MIXTURE; SILYLATION;

EID: 2942650975     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. Merino, P. Curr. Med. Chem. AIA 2002, 1, 389-411 and references cited therein.
2. (a) Giles, F.J. Expert Rev. Anticancer Ther. 2002, 2, 261-266.
3. (b) Grove, K.L.; Guo, X.; Liu, S.H.; Gao, Z.; Chu, C.K.; Cheng, Y.C. Cancer Res. 1995, 55, 3008-3011.
4. (a) Jarvis, B.; Faulds, D. Drugs 1999, 58, 101-141.
5. (b) Perry, C.M.; Faulds, D. Drugs 1997, 53, 657-680.
6. Chiacchio, U.; Corsaro, A.; Pistara, V.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R.; Grassi, G. Eur. J. Org. Chem. 2002, 1206-1212 and references cited therein.
7. (a) Merino, P.; Franco, S.; Garces, N.; Merchan, F.L.; Tejero, T. Chem. Commun. 1998, 493-494.
8. (b) Merino, P.; Franco, S.; Merchan, F.L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 3945-3949.
9. (c) Merino, P.; Franco, S.; Merchan, F.L.; Tejero, T. Tetrahedron Lett. 1998, 39, 6411-6414.
10. (d) Merino, P.; Alamo, E.M.; Bona, M.; Franco, S.; Merchan, F.L.; Tejero, T.; Vieceli, O. Tetrahedron Lett. 2000, 41, 9239-9243.
11. (e) Merino, P.; Franco, S.; Merchan, F.L.; Tejero, T. J. Org. Chem. 2000, 65, 5575-5589.
12. The addition of enolates to nitrones have been extensively studied by Trombini and coworkers: (a) Camiletti, C.; Dhavale, D.D.; Gentilucci, L.; Trombini, C. J. Chem. SOc. Perkin Trans 1 1993, 3157-3165.
13. (b) Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
14. (c) Camiletti, C.; Dhavale, D.D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293-7296
15. For other additions of ester enolates to nitrones see: (d) Kobayashi, K. ; Matoba, T.; Irisawa, S.; Takanohashi, A.; Tanmatsu, M.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 2000, 73, 2805-2809.
16. (e) Kita, Y.; Itoh, F.; Tamura, O.; Ke, Y.Y.; Tamura, Y. Tetrahedron Lett. 1987, 28, 1431-1434.
17. (f) Jost, S.; Gimbert, Y.; Greene, A.E.; Fotiadu, F. J. Org. Chem. 1997, 62, 6672-6677.
18. (g) Qian, C:; Wang, L. Tetrahedron 2000, 56, 7193-7197.
19. (h) Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S.-I. Bull. Chem. Soc. Jpn. 2000, 73, 2423-2444.
20. (i) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y. ; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888-2889.
21. DeGiorgis, F.; Lombardo, M.; Trombini, C. Synthesis, 1997, 1243-1245.