Low-valent titanium mediated reductive cleavage of O/N-trityl bonds via free radical pathway

Synthetic Communications

Volumn 32, Issue 22, 2002, Pages 3533-3540

  Rele, Shyam ^a   Nayak, Sandip K ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; AMINE; ETHER DERIVATIVE; FREE RADICAL; TITANIUM DERIVATIVE; TRITYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 0036034485     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120014795     Document Type: Article

References (28)

1. (a) Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd Ed.; John Wiley and Sons, Inc.: New York, 1991, and references cited therein;
2. (b) Kocienski, P.J. Protecting Groups; Thieme: Stuttgart, 1994.
3. (a) Nayak, S.K.; Kadam, S.M.; Banerji, A. Synlett 1993, 581;
4. (b) Kadam, S.M.; Nayak, S.K.; Banerji, A. Tetrahedron Lett. 1992, 33, 5129;
5. (c) Rele, S.; Talukdar, S.; Banerji, A. Tetrahedron Lett. 1999, 40, 767.
6. (a) McMurry, J.E. Chem. Rev. 1989, 89, 1513;
7. (b) Dushin, R.G. In Comprehensive Organometallic Chemistry II; Hegedus, L.S., Ed.; Pergamon: Oxford, 1995; Vol 12, p. 1071 and references cited therein;
8. (c) Lenoir, D. Synthesis 1989, 883;
9. (d) Furstner, A.; Bogdanovic, B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2442.
10. (a) Helferich, B. Adv. Carbohydr. Chem. 1948, 3, 79-111;
11. (b) Dekker, C.A.; Goodman, L. In Chemistry and Biochemistry; Pigman, W., Horton, D., Eds.; Academic Press: New York, London, 1970; Vol. IIA, p. 22.
12. (a) Bodanszky, M. Principles in Peptide Synthesis, 2nd Ed.; Springer-Verlag: New York, Berlin, 1993; p. 88 and references cited therein;
13. (b) Bodanszky, M.; Onetti, O.A. Peptide Synthesis; Interscience: New York, 1966, p. 36 and references cited therein.
14. (a) Hanson, R.W.; Law, H.D. J. Chem. Soc. 1965, 7285;
15. (b) Choy, Y.M.; Unrau, A.M. Carbohydr. Res. 1971, 17, 439;
16. (c) MacCoss, M.; Cameron, D. J. Carbohydr. Res. 1978, 60, 206;
17. (d) Bessodes, M.; Komiotis, D.; Antonakis, K. Tetrahedron Lett. 1986, 27, 579;
18. (e) Blickenstaff, R.T. J. Am. Chem. Soc. 1960, 82, 3673;
19. (f) Applegarth, D.A.; Buchanan, J.G.; Baddiley, J. J. Chem. Soc. 1965, 1213;
20. (g) Buchanan, J.G.; Fletcher, R. J. Chem. Soc. 1965, 6316.
21. (a) Mirrington, R.N.; Schamalzl, K.J. J. Org. Chem. 1972, 37, 2877;
22. (b) Hanessian, S.; Rancourt, G. Pure Appl. Chem. 1977, 49, 1201;
23. (c) Zervas, L.; Theodoropoulos, D.M. J. Am. Chem. Soc. 1956, 78, 1359.
24. Kovac, P.; Bauer, S. Tetrahedron Lett. 1972, 2349.
25. Dams, R.; Malinowski, M.; Westdrop, I.; Geise, H.Y. J. Org. Chem. 1982, 47, 248.
26. (a) Balu, N.; Nayak, S.K.; Banerji, A. J. Am. Chem. Soc. 1996, 118, 5932;
27. (b) Banerji, A.; Nayak, S.K. J. Chem. Soc. Chem. Commun. 1991, 1432;
28. (c) Nayak, S.K.; Banerji, A. J. Org. Chem. 1991, 56, 1940.