Synthesis of functionalized oxazolines and oxazoles with DAST and deoxo-fluor

Organic Letters

Volumn 2, Issue 8, 2000, Pages 1165-1168

  Phillips, Andrew J ^a   Uto, Yoshikazu ^a   Wipf, Peter ^a   Reno, Michael J ^b   Williams, David R ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIETHYLAMINE; DIETHYLAMINOSULFUR TRIFLUORIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FLUORINE; OXAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

DIETHYLAMINES; FLUORINE; INDICATORS AND REAGENTS; OXAZOLES;

EID: 0034689867     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005777b     Document Type: Article

References (39)

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29. 13C NMR, IR, and HRMS.
30. Although mechanistic details for reactions of alcohols with DAST are scarce, it is likely that the formation of an intermediate alkoxy-N,N-diethylaminodifluorosulfane would generate fluoride species which conceivably could be deleterious to silyl protecting groups.
31. For a related example, see: Harm, A. M.; Knight, J. G.; Stemp, G. Synlett 1996, 677.
32. 2, hexane: ethyl acetate mixtures) led to the desired oxazolines.
33. Lal, G. S.; Pez, G. P.; Pesaresi, R. J.; Prozonic, F. M.; Cheng, H. J. Org. Chem. 1999, 64, 7048. Deoxo-Fluor is commercially available from both Aldrich Chemical Co., Milwaukee, WI 53201, and Air Products and Chemicals, Allentown, PA 18195-1501.
34. 5 334.1529, found 334.1523.
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36. For a modification that allows the synthesis of some C(5)-unsubstituted oxazoles, see refs 5b and 5c.
37. Synthesized in 57% yield by the same one-pot cyclodehydration-dehydrogenation procedure from the dipeptide derived from coupling of D/L-Cbz-Val-OH and D/L-Ser-OMe·HCl.
38. R = 16.8 min.
39. 3) δ 8.29 (s, 1 H), 8.12-8.10 (m, 2 H), 7.49-7.47 (m, 3 H), 3.96 (s, 3 H). Full data: Connell, R. D.; Tebbe, M.; Gangloff, A. R.; Helquist, P.; Akermark, B. Tetrahedron 1993, 49, 5445.