Intramolecular 1,5- versus 1,6-hydrogen abstraction reaction promoted by alkoxyl radicals in pyranose and furanose models

Tetrahedron

Volumn 63, Issue 36, 2007, Pages 8910-8920

  Francisco, Cosme G ^a   Freire, Raimundo ^a   Herrera, Antonio J ^a   Pérez Martín, Inés ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 HYDROXYETHYL)GLYCOSIDE; 1,3,4,5 TETRA O ACETYL 2,8 ANHYDRO 7 DEOXY BETA DEXTRO ALTRO OCT 2 ULOPYRANOSE; 2,6 ANHYDRO 7 DEOXY 1,3,4,5 TETRA O METHYL DEXTRO GLYCERO DEXTRO MANNO OCTITOL; 2,8 ANHYDRO 1,7 DIDEOXY 3,4,5 TRI O METHYL BETA LEVO GULO OCT 2 ULOPYRANOSE; 3,6 ANHYDRO 2 DEOXY O(METHOXYMETHYL) 4,5 O METHYLEN DEXTRO ALLO HEPTITOL; 3,6 ANHYDROHEPTITOL; 3,7 ANHYDROOCTITOL; BENZENE; CARBOHYDRATE; DIACETOXYIODO BENZENE; FURAN DERIVATIVE; IODINE; METHYL 3,7 ANHYDRO 2 DEOXY 5,6,8 TRI O METHYL APHA DEXTRO MANNO OCT 4 ULOFURANOSIDE; PYRAN DERIVATIVE; RADICAL; TRI O ACETYL ANHYDRO 1,7 DIDEOXY BETA LEVO GULO OCT 2 ULOPYRANOSE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPARATIVE STUDY; INTRAMOLECULAR HYDROGEN ABSTRACTION; PRIORITY JOURNAL; THERMAL ANALYSIS;

EID: 34447625580     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.023     Document Type: Article

References (48)

1. Recent reviews:
2. Majetich G. Tetrahedron 51 (1995) 7095-7129
3. Feray L., Kuznersov N., and Renaud P. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vol. 2 (2001), Wiley-VCH, Weinheim 246-278
4. Robertson J., Pillai J., and Lush R.K. Chem. Soc. Rev. 30 (2001) 94-103
5. Martín A., Salazar J.A., and Suárez E. J. Org. Chem. 61 (1996) 3999-4006
6. Dorta R.L., Martín A., Salazar J.A., and Suárez E. J. Org. Chem. 63 (1998) 2251-2261
7. Francisco C.G., Herrera A.J., and Suárez E. J. Org. Chem. 67 (2002) 7439-7445 For a preliminary communication on this work, see:
8. Francisco C.G., Freire R., Herrera A.J., Pérez-Martín I., and Suárez E. Org. Lett. 4 (2002) 1959-1961 For other IHA reactions in carbohydrate chemistry, see:
9. Descotes G. J. Carbohydr. Chem. 7 (1988) 1-20
10. Chatgilialoglu C., Giminis T., and Spada G.P. Chem.-Eur. J. 5 (1999) 2866-2876
11. Robins M.J., Guo Z., Samano M.C., and Wnuk S.F. J. Am. Chem. Soc. 121 (1999) 1425-1433
12. Paquete L.A., Sun L.Q., Friedrich D., and Savage P.B. J. Am. Chem. Soc. 119 (1997) 8438-8450
13. Bruke S.D., Kort M.E., Strickland S.M.S., Organ H.M., and Silks L.A. Tetrahedron Lett. 35 (1994) 1503-1506
14. Hatakeyama S., Kawamura M., and Takano S. J. Am. Chem. Soc. 116 (1994) 4081-4082
15. Danishefsky S.J., Armistead D.A., Wincott F.E., Selnick H.G., and Hungate R. J. Am. Chem. Soc. 111 (1989) 2967-2980
16. Brimble M.A., and Farès F.A. Tetrahedron 55 (1999) 7661-7706
17. Concepción J.I., Francisco C.G., Hernández R., Salazar J.A., and Suárez E. Tetrahedron Lett. 25 (1984) 1953-1984
18. HAT reaction through eight-membered transition states or higher promoted by alkoxyl radicals which suffer a severe entropic penalty are practically unknown. Recently an IHA through a nine-membered transition state between glucopyranose units in a disaccharide model has been observed in this laboratory:. Francisco C.G., Herrera A.J., Kennedy A.R., Melián D., and Suárez E. Angew. Chem., Int. Ed. 41 (2002) 860-862
19. CRC Handbook of Chemistry and Physics. 73rd ed. (1992), CRC, Boca Raton, FL pp 9-138
20. González C.C., Kennedy A.R., León E.I., Riesco-Fagundo C., and Suárez E. Angew. Chem., Int. Ed. 40 (2001) 2326-2328
21. Francisco C.G., González C.C., and Suárez E. J. Org. Chem. 63 (1998) 8092-8093
22. An example of the influence of the substituents on the 1,5-HAT reaction compared with competing β-fragmentation of alkoxyl radicals has been published:. Allen P.R., Brimble M.A., and Farès F.A. J. Chem. Soc., Perkin Trans. 1 (1998) 2403-2411
23. No products arising from the geometrically possible abstraction of the hydrogen at C5 have been detected in the examples described in this work. Probably the abstraction at this position is disfavoured by steric and stereoelectronic factors. For studies of stereoelectronic effects in intramolecular hydrogen abstraction reactions, see:
24. Malatesta V., and Ingold K.U. J. Am. Chem. Soc. 103 (1981) 609-614
25. Beckwith A.L.J., and Easton C.J. J. Am. Chem. Soc. 103 (1981) 615-619
26. For competition between 1-5-, 1-6- and 1-7-hydrogen transfer, see:. Denenmark D., Winkler T., Waldner A., and De Mesmaeker A. Tetrahedron Lett. 33 (1992) 3613-3616
27. Satake M., Ofuji K., Naoki H., James K.J., Furey A., McMahon T., Silke J., and Yasumoto T. J. Am. Chem. Soc. 120 (1998) 9967-9968
28. Aiguade J., Hao J., and Forsyth C.J. Org. Lett. 3 (2001) 979-982
29. Nicolaou K.C., Oihko P.N., Diedrichs N., Zou N., and Bernal F. Angew. Chem., Int. Ed. 40 (2001) 1262-1265
30. Li X.-L., Cheng X., Yang L.M., Wang R.-R., Zheng Y.-T., Xiao W.-L., Zhao Y., Xu G., Lu Y., Chang Y., Zheng Q.-T., Zhao Q.-S., and Sun H.-D. Org. Lett. 8 (2006) 1937-1940
31. Yamada M., Hayashi K.-I., Ikeda S., Tsutsui K., Tsutsui K., Ito T., Iinuma M., and Nozaki H. Biol. Pharm. Bull. 29 (2006) 1504-1507
32. Perlmutter P., Selajerern W., and Vounatsos F. Org. Biomol. Chem. 2 (2004) 2220-2228
33. Luengo J.I., and Gleason J.G. Tetrahedron Lett. 33 (1992) 6911-6914
34. Richter P.K., Tomaszewski M.J., Miller R.A., Patron A.P., and Nicolaou K.C. J. Chem. Soc., Chem. Commun. (1994) 1151-1152
35. Evidence for a deactivating influence of the β-oxygen on the intermolecular hydrogen abstraction reaction has been described:
36. Busfield W.K., Grice I.D., Jenkins I.D., and Monteiro M.J. J. Chem. Soc., Perkin Trans. 2 (1994) 1071-1077
37. Busfield W.K., Grice I.D., Jenkins I.D., and Monteiro M.J. J. Chem. Soc., Perkin Trans. 2 (1994) 1079-1086
38. An example of a double IHA reaction: {A figure is presented}For other double IHA reactions in carbohydrate models, see Ref. 2a,b.
39. For studies of the influence of polar factors on, see:
40. Beckwith A.L.J., Zavitsas A.A., and Chatgilialoglu C. J. Am. Chem. Soc. 117 (1995) 10645-10654
41. Kaushal P., Mok P.L.H., and Roberts B.P. J. Chem. Soc., Perkin Trans. 2 (1990) 1663-1670 For an example of correlation between proximity in the ground state and regioselectivity in an IHA reaction, see Ref. 3b
42. Bicyclic ketals can be easily converted into the corresponding bicyclic ethers by stereoselective reduction:
43. Takemoto Y., Furuse S.-I., Hayase H., Echigo T., Iwata C., Tanaka T., and Ibuka T. Chem. Commun. (1999) 2515-2516
44. Nicolaou K.C., Hwang C.-K., and Nugiel D.A. J. Am. Chem. Soc. 111 (1989) 4136-4137
45. Giannis A., and Sandhoff K. Tetrahedron Lett. 26 (1985) 1479-1482
46. Miljkovic M., and Habash-Marino M. J. Org. Chem. 48 (1983) 855-860
47. Beckwith A.L.J., and Duggan P.J. J. Chem. Soc., Perkin Trans. 2 (1993) 1673-1680
48. Francisco C.G., Herrera A.J., and Suárez E. J. Org. Chem. 68 (2003) 1012-1017