Israel journal of chemistry

A discriminating protecting group strategy for alcohols and amines

LJ Liotta, B Ganem

Index: Liotta, Louis J.; Ganem, Bruce Israel Journal of Chemistry, 1991 , vol. 31, # 3 p. 215 - 222

Full Text: HTML

Citation Number: 4

Abstract

Abstract The protection of alcohols and amines as O-and N-benzyl derivatives has long played a central role in organic synthesis. For cases where the conventional method of benzylation under strongly basic conditions is not applicable, we now describe an alternate method using phenyldiazomethane that proceeds under near-neutral conditions with HBF 4 as a catalyst. O-Benzylation occurs at− 40 C and works well on primary, secondary, and ...

~90%

~13%

~5%

~4%

~87%

~60%

Complexes of borane and N-heterocyclic carbenes: a new class...

[Ueng, Shau-Hua; Brahmi, Malika Makhlouf; Derat, Etienne; Fensterbank, Louis; Lacote, Emmanuel; Malacria, Max; Curran, Dennis P. Journal of the American Chemical Society, 2008 , vol. 130, # 31 p. 10082 - 10083]

Benzylation of Alcoholic Hydroxyl Groups with Benzyl Mesylat...

[Nakano, Masakazu; Matsuo, Jun-Ichi; Mukaiyama, Teruaki Chemistry Letters, 2000 , # 12 p. 1352 - 1353]

Benzylation of alcohols by using bis [acetylacetonato] coppe...

[Sirkecioglu, Okan; Karliga, Bekir; Talinli, Naciye Tetrahedron Letters, 2003 , vol. 44, # 46 p. 8483 - 8485]

Palladium catalyzed cross-coupling and tandem cyclization-co...

[Bhatt; Shin, Dong-Soo; Falck; Mioskowski, Charles Tetrahedron Letters, 1992 , vol. 33, # 34 p. 4885 - 4888]

Boryltrihydroborate: synthesis, structure, and reactivity as...

[Nozaki, Kyoko; Aramaki, Yoshitaka; Yamashita, Makoto; Ueng, Shau-Hua; Malacria, Max; Lacote, Emmanuel; Curran, Dennis P. Journal of the American Chemical Society, 2010 , vol. 132, # 33 p. 11449 - 11451]