Synthesis and applications of fluorous silyl protecting groups with improved acid stability

Tetrahedron Letters

Volumn 40, Issue 31, 1999, Pages 5667-5670

  Röver, Stephan ^a   Wipf, Peter ^b  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ETHER DERIVATIVE; SILANE DERIVATIVE; SILICA GEL;

ARTICLE; CHEMICAL LABELING; LIQUID LIQUID EXTRACTION; MOLECULAR STABILITY; PURIFICATION; SOLID PHASE EXTRACTION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033618301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01106-5     Document Type: Article

References (19)

1. (a) Curran, D. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1174.
2. (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
3. (c) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
4. (d) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
5. (a) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714.
6. (b) Billiet, H. A. H.; Schoenmakers, P. J.; de Galan, L. J. Chromatogr. 1981, 218, 443.
7. (c) Sadek, P. C.; Carr, P. W. J. Chromatogr. 1984, 288, 25.
8. (d) Danielson, N. D.; Beaver, L. G.; Wangsa, J. J. Chromatogr. 1991, 544, 187.
9. (a) Boutevin, B.; Guida-Pietrasanta, F.; Ratsimihety, A.; Caporiccio, G.; Gornowicz, G. J. J. Fluorine Chem. 1993, 60, 211.
10. (b) Wipf, P.; Reeves, J. Tetrahedron Lett. 1999, 40, 4649.
11. (c) Wipf, P.; Reeves, J. Tetrahedron Lett. 1999, in press.
12. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley-Interscience: New York, 1991, and references cited therein.
13. (a) Gillard, J. W.; Fortin, R.; Morton, H. E.; Yoakim, C.; Quesnelle, C. A.; Daignault, S.; Guindon, Y. J. Org. Chem. 1988, 53, 2602.
14. (b) Guindon, Y.; Fortin, R.; Yoakim, C.; Gillard, J. W. Tetrahedron Lett. 1984, 25, 4717.
15. +, 4), 1185 (5), 1126 (85).
16. 3) § 135.5, 132.3, 129.9, 127.8, 125-105 (m, 8C), 71.1, 55.7, 35.7, 34.1 (b), 26.1, 25.6, 23.7, 18.8; HRMS(EI) m/z found 723.1597; calcd 723.1587.
17. t [min]: 2.6 (5a), 2.9 (5b), 2.3 (8a); Novapak C18, 3.9x150 mm, 1.2 mL/min, MeOH as eluent).
18. 2.
19. 2 cartridge.