Stereospecific β-Lithiation of Oxazolinyloxiranes: Synthesis of α,β-Epoxy-γ-butyrolactones

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1551-1554

  Capriati, Vito ^a   Degennaro, Leonardo ^a   Favia, Raffaele ^a   Florio, Saverio ^a   Luisi, Renzo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; EPOXIDE; GAMMA BUTYROLACTONE; LITHIUM;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIZATION; EPOXY COMPOUNDS; LITHIUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 0037007713     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025781i     Document Type: Article

References (15)

1. Kuramochi, K.; Itaya, H.; Nagata, S.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 7367-7370.
2. Mani, N. S.; Townsend, C. A. J. Org. Chem. 1997, 62, 636-640.
3. Lertvorachon, J.; Thebtaranonth, Y.; Thongpanchang, T.; Thonyoo, P. J. Org. Chem. 2001, 66, 4692-4694.
4. Abbotto, A.; Capriati, V.; Degennaro L.; Florio, S.; Luisi, R.; Pierrot, M.; Salomone, A. J. Org. Chem. 2001, 66, 3049-3058 and references therein.
5. Relative configuration, distinguishing diastereoisomers, may be denoted by the configurational descriptors R*,R* and R*,S* meaning, respectively, that the two centres have identical or opposite configurations, as reported in: IUPAC. Nomenclature of Organic Chemistry, Sections A-F and H; Pergamon Press: Elmsford, NY, 1979; p 482, Rule E-4.10.
6. Capriati, V.; Degennaro, L.; Florio S.; Luisi, R.; Tralli, C.; Troisi, L. Synthesis 2001, 15, 2299-2306.
7. Kingsbury, C. A.; Durham, D. L.; Hutton, R. J. Org. Chem. 1978, 43, 4696-4700.
8. Eisch, J. J.; Galle, J. E. J. Org. Chem. 1990, 55, 4835-4840.
9. Lertvorachon, J.; Thebtaranonth, Y.; Thongpanchang, T.; Thongyoo, P. J. Org. Chem. 2001, 66, 4692-4694.
10. Generation and stereospecific alkylation of an optically active α-trifluoromethyl oxiranyl anion has also been recently reported: Yamauchi, Y.; Katagiri, T.; Uneyama, K. Org. Lett. 2002, 4, 173-176.
11. Florio, S.; Capriati, V.; Luisi, R. Eur. J. Org. Chem. 2001, 2035-2038.
12. Florio, S.; Capriati, V.; Luisi, R.; Abbotto, A.; Pippel, D. J. Tetrahedron 2001, 57, 6775-6786.
13. Crystallographic data for compound 7 have been deposited at the Cambridge Crystallographic Data Centre (deposition no. CCDC-179557). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [fax: (int.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk]. ORTEP view and CIF file for compound 7 have been also reported as Supporting Information.
14. 3- CHO) as well as of the corresponding epoxylactones 4g.
15. 3-CHO) as well as of the corresponding epoxylactones 4g.