Mild and chemoselective catalytic deprotection of ketals and acetals using cerium(IV) ammonium nitrate

Tetrahedron

Volumn 59, Issue 45, 2003, Pages 8989-8999

  Ates, Ali ^a   Gautier, Arnaud ^a   Leroy, Bernard ^a   Plancher, Jean Marc ^a   Quesnel, Yannick ^a   Vanherck, Jean Christophe ^a   Markó, István E ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Acetals; Catalysis; Cerium and compounds; Deprotection; Ketals

Indexed keywords

ACETAL DERIVATIVE; AMMONIUM DERIVATIVE; CERIUM AMMONIUM NITRATE; LEWIS ACID; NITRIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DEPROTECTION REACTION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0142186276     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.03.002     Document Type: Article

References (72)

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8. For some selected references, see: (a) Ballou C.E., Fischer H.O.L. J. Am. Chem. Soc. 78:1956;1659 (b) Showler A.J., Darley P.A. Chem. Rev. 67:1967;427 (c) Huet F., Lechevallier A., Pellet M., Conia J.M. Synthesis. 1978;63 (d) Bauduin G., Bondon D., Pietrasanta Y., Pucci B. Tetrahedron. 34:1978;3269 (e) Evans D.A., Tanis S.P., Hart. J. Am. Chem. Soc. 103:1981;5813 (f) Cappola G.M. Synthesis. 1984;1021 (g) Tufariello J.J., Winzenberg K. Tetrahedron Lett. 27:1986;1645 (h) Stern A.J., Swenton J.S. J. Org. Chem. 54:1989;2953 (i) Lee A.S.-Y., Yeh H.-C., Tsai M.-H. Tetrahedron Lett. 36:1995;6891 (j) Lee A.S.-Y., Cheng C.-L. Tetrahedron. 53:1997;14255.
9. For some selected references, see: (a) Ballou C.E., Fischer H.O.L. J. Am. Chem. Soc. 78:1956;1659 (b) Showler A.J., Darley P.A. Chem. Rev. 67:1967;427 (c) Huet F., Lechevallier A., Pellet M., Conia J.M. Synthesis. 1978;63 (d) Bauduin G., Bondon D., Pietrasanta Y., Pucci B. Tetrahedron. 34:1978;3269 (e) Evans D.A., Tanis S.P., Hart. J. Am. Chem. Soc. 103:1981;5813 (f) Cappola G.M. Synthesis. 1984;1021 (g) Tufariello J.J., Winzenberg K. Tetrahedron Lett. 27:1986;1645 (h) Stern A.J., Swenton J.S. J. Org. Chem. 54:1989;2953 (i) Lee A.S.-Y., Yeh H.-C., Tsai M.-H. Tetrahedron Lett. 36:1995;6891 (j) Lee A.S.-Y., Cheng C.-L. Tetrahedron. 53:1997;14255.
10. For some selected references, see: (a) Ballou C.E., Fischer H.O.L. J. Am. Chem. Soc. 78:1956;1659 (b) Showler A.J., Darley P.A. Chem. Rev. 67:1967;427 (c) Huet F., Lechevallier A., Pellet M., Conia J.M. Synthesis. 1978;63 (d) Bauduin G., Bondon D., Pietrasanta Y., Pucci B. Tetrahedron. 34:1978;3269 (e) Evans D.A., Tanis S.P., Hart. J. Am. Chem. Soc. 103:1981;5813 (f) Cappola G.M. Synthesis. 1984;1021 (g) Tufariello J.J., Winzenberg K. Tetrahedron Lett. 27:1986;1645 (h) Stern A.J., Swenton J.S. J. Org. Chem. 54:1989;2953 (i) Lee A.S.-Y., Yeh H.-C., Tsai M.-H. Tetrahedron Lett. 36:1995;6891 (j) Lee A.S.-Y., Cheng C.-L. Tetrahedron. 53:1997;14255.
11. For some selected references, see: (a) Ballou C.E., Fischer H.O.L. J. Am. Chem. Soc. 78:1956;1659 (b) Showler A.J., Darley P.A. Chem. Rev. 67:1967;427 (c) Huet F., Lechevallier A., Pellet M., Conia J.M. Synthesis. 1978;63 (d) Bauduin G., Bondon D., Pietrasanta Y., Pucci B. Tetrahedron. 34:1978;3269 (e) Evans D.A., Tanis S.P., Hart. J. Am. Chem. Soc. 103:1981;5813 (f) Cappola G.M. Synthesis. 1984;1021 (g) Tufariello J.J., Winzenberg K. Tetrahedron Lett. 27:1986;1645 (h) Stern A.J., Swenton J.S. J. Org. Chem. 54:1989;2953 (i) Lee A.S.-Y., Yeh H.-C., Tsai M.-H. Tetrahedron Lett. 36:1995;6891 (j) Lee A.S.-Y., Cheng C.-L. Tetrahedron. 53:1997;14255.
12. For some selected references, see: (a) Ballou C.E., Fischer H.O.L. J. Am. Chem. Soc. 78:1956;1659 (b) Showler A.J., Darley P.A. Chem. Rev. 67:1967;427 (c) Huet F., Lechevallier A., Pellet M., Conia J.M. Synthesis. 1978;63 (d) Bauduin G., Bondon D., Pietrasanta Y., Pucci B. Tetrahedron. 34:1978;3269 (e) Evans D.A., Tanis S.P., Hart. J. Am. Chem. Soc. 103:1981;5813 (f) Cappola G.M. Synthesis. 1984;1021 (g) Tufariello J.J., Winzenberg K. Tetrahedron Lett. 27:1986;1645 (h) Stern A.J., Swenton J.S. J. Org. Chem. 54:1989;2953 (i) Lee A.S.-Y., Yeh H.-C., Tsai M.-H. Tetrahedron Lett. 36:1995;6891 (j) Lee A.S.-Y., Cheng C.-L. Tetrahedron. 53:1997;14255.
13. For some selected references, see: (a) Ballou C.E., Fischer H.O.L. J. Am. Chem. Soc. 78:1956;1659 (b) Showler A.J., Darley P.A. Chem. Rev. 67:1967;427 (c) Huet F., Lechevallier A., Pellet M., Conia J.M. Synthesis. 1978;63 (d) Bauduin G., Bondon D., Pietrasanta Y., Pucci B. Tetrahedron. 34:1978;3269 (e) Evans D.A., Tanis S.P., Hart. J. Am. Chem. Soc. 103:1981;5813 (f) Cappola G.M. Synthesis. 1984;1021 (g) Tufariello J.J., Winzenberg K. Tetrahedron Lett. 27:1986;1645 (h) Stern A.J., Swenton J.S. J. Org. Chem. 54:1989;2953 (i) Lee A.S.-Y., Yeh H.-C., Tsai M.-H. Tetrahedron Lett. 36:1995;6891 (j) Lee A.S.-Y., Cheng C.-L. Tetrahedron. 53:1997;14255.
14. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
15. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
16. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
17. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
18. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
19. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
20. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
21. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
22. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
23. For some pertinent references, see: (a) Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Tagarelli A., Sindona G., Bartoli G.J. J. Org. Chem. 67:2002;9093 (b) Carrigan M.D., Sarapa D., Dusan S., Russell C., Wieland L.C., Mohan R.S. J. Org. Chem. 67:2002;1027 (c) Kantam M.L., Neeraja V., Sreekanth P. Catal. Commun. 2:2001;301 (d) Heravi M.M., Tajbakhsh M., Habibzadeh S., Ghassemzadeh M. Monatsh. Fur Chem. 132:2001;985 (e) Ko K.-Y., Park S.-T., Choi M.-J. Bull. Korean Chem. Soc. 21:2000;951 (f) Eash K.J., Pulia M.S., Wieland L.C., Mohan R.S. J. Org. Chem. 65:2000;8399 (g) Ko K.-Y., Park S.-T. Tetrahedron Lett. 40:1999;6025 (h) Firouzabadi H., Iranpoor N., Karimi B. J. Chem. Res., Synop. 1998;664 (i) Kaur G., Trehan A., Trehan S. J. Org. Chem. 63:1998;2365 (j) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem. 38B:1999;1234.
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36. The deep colour that develops during these reactions is probably due to some charge-transfer complexes between CAN and the ketal protecting group. A solution of CAN in water or in water/MeCN is slightly yellow-coloured. For the formation of red-tinged complexes between CAN and alcohols, see: (a) Littler J.-S., Waters W.A. J. Chem. Soc. 1960;2767 (b) Young L.B., Trahanovsky W.S. J. Am. Chem. Soc. 91:1969;5060. For electron-transfer reactions involving CAN, see: (c) Baciocchi E., Giacco T.D., Rol C., Sebastiani G.V. Tetrahedron Lett. 30:1989;3573. A plausible mechanism rationalising the deprotection of acetals/ketals using 2.5 equiv. of CAN can be formulated as shown in Figure 9.
37. The deep colour that develops during these reactions is probably due to some charge-transfer complexes between CAN and the ketal protecting group. A solution of CAN in water or in water/MeCN is slightly yellow-coloured. For the formation of red-tinged complexes between CAN and alcohols, see: (a) Littler J.-S., Waters W.A. J. Chem. Soc. 1960;2767 (b) Young L.B., Trahanovsky W.S. J. Am. Chem. Soc. 91:1969;5060. For electron-transfer reactions involving CAN, see: (c) Baciocchi E., Giacco T.D., Rol C., Sebastiani G.V. Tetrahedron Lett. 30:1989;3573. A plausible mechanism rationalising the deprotection of acetals/ketals using 2.5 equiv. of CAN can be formulated as shown in Figure 9.
38. The deep colour that develops during these reactions is probably due to some charge-transfer complexes between CAN and the ketal protecting group. A solution of CAN in water or in water/MeCN is slightly yellow-coloured. For the formation of red-tinged complexes between CAN and alcohols, see: (a) Littler J.-S., Waters W.A. J. Chem. Soc. 1960;2767 (b) Young L.B., Trahanovsky W.S. J. Am. Chem. Soc. 91:1969;5060. For electron-transfer reactions involving CAN, see: (c) Baciocchi E., Giacco T.D., Rol C., Sebastiani G.V. Tetrahedron Lett. 30:1989;3573. A plausible mechanism rationalising the deprotection of acetals/ketals using 2.5 equiv. of CAN can be formulated as shown in Figure 9.
39. Ho T.-L., Ho C.H., Wong C.M. J. Chem. Soc. Chem. Commun. 1972;791.
40. DattaGupta A., Singh R., Singh V.K. Synlett. 1996;69.
41. (a) Hwu J.R., Jain M.L., Tsay S.-C., Hakimelahi G.H. Tetrahedron Lett. 37:1996;2035.
42. For other deprotections using CAN, see: (b) Schreiber S.L., Kiesling L.L. Tetrahedron Lett. 30:1989;433 (c) Matsumoto T., Katsuki M., Jona H., Suzuki K. J. Am. Chem. Soc. 113:1991;6982 (d) Cotelle P., Catteau J.-P. Tetrahedron Lett. 33:1992;3855 (e) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem., Sect. B: Org. Chem. Med. Chem. 38B:1999;1234 (f) Hwu J.R., Jain M.L., Tsai F.-Y., Tsay S.-C., Balakumar A., Hakimelahi G.H. J. Org. Chem. 65:2000;5077 (g) Roy S.C., Banerjee B. Synlett. 2002;1677 (h) Hwu J.R., Jain M.L., Tsai F.-Y., Balakumar A., Hakimelahi G.H., Tsay S.-C. Arkivoc. 9:2002;29.
43. For other deprotections using CAN, see: (b) Schreiber S.L., Kiesling L.L. Tetrahedron Lett. 30:1989;433 (c) Matsumoto T., Katsuki M., Jona H., Suzuki K. J. Am. Chem. Soc. 113:1991;6982 (d) Cotelle P., Catteau J.-P. Tetrahedron Lett. 33:1992;3855 (e) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem., Sect. B: Org. Chem. Med. Chem. 38B:1999;1234 (f) Hwu J.R., Jain M.L., Tsai F.-Y., Tsay S.-C., Balakumar A., Hakimelahi G.H. J. Org. Chem. 65:2000;5077 (g) Roy S.C., Banerjee B. Synlett. 2002;1677 (h) Hwu J.R., Jain M.L., Tsai F.-Y., Balakumar A., Hakimelahi G.H., Tsay S.-C. Arkivoc. 9:2002;29.
44. For other deprotections using CAN, see: (b) Schreiber S.L., Kiesling L.L. Tetrahedron Lett. 30:1989;433 (c) Matsumoto T., Katsuki M., Jona H., Suzuki K. J. Am. Chem. Soc. 113:1991;6982 (d) Cotelle P., Catteau J.-P. Tetrahedron Lett. 33:1992;3855 (e) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem., Sect. B: Org. Chem. Med. Chem. 38B:1999;1234 (f) Hwu J.R., Jain M.L., Tsai F.-Y., Tsay S.-C., Balakumar A., Hakimelahi G.H. J. Org. Chem. 65:2000;5077 (g) Roy S.C., Banerjee B. Synlett. 2002;1677 (h) Hwu J.R., Jain M.L., Tsai F.-Y., Balakumar A., Hakimelahi G.H., Tsay S.-C. Arkivoc. 9:2002;29.
45. For other deprotections using CAN, see: (b) Schreiber S.L., Kiesling L.L. Tetrahedron Lett. 30:1989;433 (c) Matsumoto T., Katsuki M., Jona H., Suzuki K. J. Am. Chem. Soc. 113:1991;6982 (d) Cotelle P., Catteau J.-P. Tetrahedron Lett. 33:1992;3855 (e) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem., Sect. B: Org. Chem. Med. Chem. 38B:1999;1234 (f) Hwu J.R., Jain M.L., Tsai F.-Y., Tsay S.-C., Balakumar A., Hakimelahi G.H. J. Org. Chem. 65:2000;5077 (g) Roy S.C., Banerjee B. Synlett. 2002;1677 (h) Hwu J.R., Jain M.L., Tsai F.-Y., Balakumar A., Hakimelahi G.H., Tsay S.-C. Arkivoc. 9:2002;29.
46. For other deprotections using CAN, see: (b) Schreiber S.L., Kiesling L.L. Tetrahedron Lett. 30:1989;433 (c) Matsumoto T., Katsuki M., Jona H., Suzuki K. J. Am. Chem. Soc. 113:1991;6982 (d) Cotelle P., Catteau J.-P. Tetrahedron Lett. 33:1992;3855 (e) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem., Sect. B: Org. Chem. Med. Chem. 38B:1999;1234 (f) Hwu J.R., Jain M.L., Tsai F.-Y., Tsay S.-C., Balakumar A., Hakimelahi G.H. J. Org. Chem. 65:2000;5077 (g) Roy S.C., Banerjee B. Synlett. 2002;1677 (h) Hwu J.R., Jain M.L., Tsai F.-Y., Balakumar A., Hakimelahi G.H., Tsay S.-C. Arkivoc. 9:2002;29.
47. For other deprotections using CAN, see: (b) Schreiber S.L., Kiesling L.L. Tetrahedron Lett. 30:1989;433 (c) Matsumoto T., Katsuki M., Jona H., Suzuki K. J. Am. Chem. Soc. 113:1991;6982 (d) Cotelle P., Catteau J.-P. Tetrahedron Lett. 33:1992;3855 (e) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem., Sect. B: Org. Chem. Med. Chem. 38B:1999;1234 (f) Hwu J.R., Jain M.L., Tsai F.-Y., Tsay S.-C., Balakumar A., Hakimelahi G.H. J. Org. Chem. 65:2000;5077 (g) Roy S.C., Banerjee B. Synlett. 2002;1677 (h) Hwu J.R., Jain M.L., Tsai F.-Y., Balakumar A., Hakimelahi G.H., Tsay S.-C. Arkivoc. 9:2002;29.
48. For other deprotections using CAN, see: (b) Schreiber S.L., Kiesling L.L. Tetrahedron Lett. 30:1989;433 (c) Matsumoto T., Katsuki M., Jona H., Suzuki K. J. Am. Chem. Soc. 113:1991;6982 (d) Cotelle P., Catteau J.-P. Tetrahedron Lett. 33:1992;3855 (e) Nair V., Nair L.G., Balagopal L., Rajan R. Indian J. Chem., Sect. B: Org. Chem. Med. Chem. 38B:1999;1234 (f) Hwu J.R., Jain M.L., Tsai F.-Y., Tsay S.-C., Balakumar A., Hakimelahi G.H. J. Org. Chem. 65:2000;5077 (g) Roy S.C., Banerjee B. Synlett. 2002;1677 (h) Hwu J.R., Jain M.L., Tsai F.-Y., Balakumar A., Hakimelahi G.H., Tsay S.-C. Arkivoc. 9:2002;29.
49. The discrepancy between the yields of the crude products and the pure samples mostly reflects the mechanical losses encountered during the purification step (volatility) or the instability of the compounds towards the support used for the chromatography. In general, the crude products are sufficiently pure (>95% purity) to be used as such in a subsequent transformation.
50. 3, see: (c) Marcantoni E., Nobili F., Bartoli G., Bosco M., Sambri L. J. Org. Chem. 62:1997;4183. For the selective CAN-mediated deprotection of TBS ethers in the presence of ketals, in MeOH/water, see Ref. 13.
51. 3, see: (c) Marcantoni E., Nobili F., Bartoli G., Bosco M., Sambri L. J. Org. Chem. 62:1997;4183. For the selective CAN-mediated deprotection of TBS ethers in the presence of ketals, in MeOH/water, see Ref. 13.
52. 3, see: (c) Marcantoni E., Nobili F., Bartoli G., Bosco M., Sambri L. J. Org. Chem. 62:1997;4183. For the selective CAN-mediated deprotection of TBS ethers in the presence of ketals, in MeOH/water, see Ref. 13.
53. For example, attempted purification of hydroxyketone 29 by silica gel column chromatography resulted in its rapid transformation into enone 30.
54. (a) Ho T.L. Synthesis. 1978;936.
55. (b) Olah G.A., Gupta B.G.B., Fung A.P. Synthesis. 1980;897
56. (c) Tomioka H., Oshima K., Nozaki H. Tetrahedron Lett. 23:1982;539.
57. Using 2.5 equiv. of CAN or a variety of acid catalysts, complete epimerisation of 44 occurs, affording a near thermodynamic mixture of axial and equatorial product in a ratio of 60/40. This experiment is a clear testimony to the lenient reaction conditions prevailing in our catalytic procedure.
58. Under acidic conditions, a competitive fragmentation of the spiro bicyclic system has been observed, leading to the corresponding cyclohexanone derivative bearing at the α-position a 2′-hydroxyethyl-4-butanoic ester side chain.
59. The CAN/py (pH 4.4) system has been discovered in this laboratory by Dr Ali Ates during the mechanistic study of the CAN-catalysed deprotection of 21 . These results have been communicated in all good faith to Dr Manzo, E. (visiting scientist) and Professor Parrilli, M. who subsequently published them Manzo E., Barone G., Bedini E., Iadonisi A., Mangoni L., Parrilli M. Tetrahedron. 58:2002;129. and Ref. 16b.
60. For the selective cleavage of trityl ethers, see: (a) Yadav J.S., Reddy B.V.S. Synlett. 2000;1275 (b) Yadav J.S., Reddy B.V.S. Carbohydr. Res. 329:2000;885 (c) Lu R.J., Liu D., Giese R.W. Tetrahedron Lett. 41:2000;2817. For the selective deprotection of ketals in the presence of trityl ethers, see: (d) Markó I.E., Ates A., Augustyns B., Gautier A., Quesnel Y., Turet L., Wiaux M. Tetrahedron Lett. 40:1999;5613 (e) Sabitha G., Babu R.S., Rajkumar M., Srividya R., Yadav J.S. Org. Lett. 3:2001;1119 (f) Xiao X., Bai D. Synlett. 2001;535.
61. For the selective cleavage of trityl ethers, see: (a) Yadav J.S., Reddy B.V.S. Synlett. 2000;1275 (b) Yadav J.S., Reddy B.V.S. Carbohydr. Res. 329:2000;885 (c) Lu R.J., Liu D., Giese R.W. Tetrahedron Lett. 41:2000;2817. For the selective deprotection of ketals in the presence of trityl ethers, see: (d) Markó I.E., Ates A., Augustyns B., Gautier A., Quesnel Y., Turet L., Wiaux M. Tetrahedron Lett. 40:1999;5613 (e) Sabitha G., Babu R.S., Rajkumar M., Srividya R., Yadav J.S. Org. Lett. 3:2001;1119 (f) Xiao X., Bai D. Synlett. 2001;535.
62. For the selective cleavage of trityl ethers, see: (a) Yadav J.S., Reddy B.V.S. Synlett. 2000;1275 (b) Yadav J.S., Reddy B.V.S. Carbohydr. Res. 329:2000;885 (c) Lu R.J., Liu D., Giese R.W. Tetrahedron Lett. 41:2000;2817. For the selective deprotection of ketals in the presence of trityl ethers, see: (d) Markó I.E., Ates A., Augustyns B., Gautier A., Quesnel Y., Turet L., Wiaux M. Tetrahedron Lett. 40:1999;5613 (e) Sabitha G., Babu R.S., Rajkumar M., Srividya R., Yadav J.S. Org. Lett. 3:2001;1119 (f) Xiao X., Bai D. Synlett. 2001;535.
63. For the selective cleavage of trityl ethers, see: (a) Yadav J.S., Reddy B.V.S. Synlett. 2000;1275 (b) Yadav J.S., Reddy B.V.S. Carbohydr. Res. 329:2000;885 (c) Lu R.J., Liu D., Giese R.W. Tetrahedron Lett. 41:2000;2817. For the selective deprotection of ketals in the presence of trityl ethers, see: (d) Markó I.E., Ates A., Augustyns B., Gautier A., Quesnel Y., Turet L., Wiaux M. Tetrahedron Lett. 40:1999;5613 (e) Sabitha G., Babu R.S., Rajkumar M., Srividya R., Yadav J.S. Org. Lett. 3:2001;1119 (f) Xiao X., Bai D. Synlett. 2001;535.
64. For the selective cleavage of trityl ethers, see: (a) Yadav J.S., Reddy B.V.S. Synlett. 2000;1275 (b) Yadav J.S., Reddy B.V.S. Carbohydr. Res. 329:2000;885 (c) Lu R.J., Liu D., Giese R.W. Tetrahedron Lett. 41:2000;2817. For the selective deprotection of ketals in the presence of trityl ethers, see: (d) Markó I.E., Ates A., Augustyns B., Gautier A., Quesnel Y., Turet L., Wiaux M. Tetrahedron Lett. 40:1999;5613 (e) Sabitha G., Babu R.S., Rajkumar M., Srividya R., Yadav J.S. Org. Lett. 3:2001;1119 (f) Xiao X., Bai D. Synlett. 2001;535.
65. For the selective cleavage of trityl ethers, see: (a) Yadav J.S., Reddy B.V.S. Synlett. 2000;1275 (b) Yadav J.S., Reddy B.V.S. Carbohydr. Res. 329:2000;885 (c) Lu R.J., Liu D., Giese R.W. Tetrahedron Lett. 41:2000;2817. For the selective deprotection of ketals in the presence of trityl ethers, see: (d) Markó I.E., Ates A., Augustyns B., Gautier A., Quesnel Y., Turet L., Wiaux M. Tetrahedron Lett. 40:1999;5613 (e) Sabitha G., Babu R.S., Rajkumar M., Srividya R., Yadav J.S. Org. Lett. 3:2001;1119 (f) Xiao X., Bai D. Synlett. 2001;535.
66. Majewsky M., MacKinnon J. Can. J. Chem. 72:1994;1699.
67. Ballester P., Garcia-Raso A., Mestres R. Synthesis. 1985;802.
68. Kopecky K.R., Lockwood P.A., Gomez R.R., Ding J.-Y. Can. J. Chem. 59:1981;851.
69. Williams J.R., Sarkisian G.M. J. Org. Chem. 37:1972;4463.
70. Bozó E., Boros S., Kuszmann J., Gács-Baitz E., Párkányi L. Carbohydr. Res. 308:1998;297.
71. (a) Brimacombe J.S., Miller J.A., Zakir U. Carbohydr. Res. 49:1976;233.
72. (b) Redlich H., Samm K., Lenfers J.B., Bruns W. Carbohydr. Res. 174:1988;341.