Tetrahedron

Pd/C (en)-Catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations

K Hattori, H Sajiki, K Hirota

Index: Hattori, Kazuyuki; Sajiki, Hironao; Hirota, Kosaku Tetrahedron, 2000 , vol. 56, # 43 p. 8433 - 8441

Full Text: HTML

Citation Number: 68

Abstract

A chemoselective method for the hydrogenation of acetylene, olefin, azide, nitro and benzyl ester functionalities with retention of the aliphatic N-Cbz group was established. The chemoselectivity was accomplished by using a combination of 5% Pd/C–ethylenediamine [5% Pd/C (en)] and THF (or 1, 4-dioxane) as a solvent, and the scope and limitations of this methodology were investigated. These results reinforce the utility of N-Cbz protective ...

~88%

~97%

~99%

~99%

~64%

~99%

~24%

~78%

~76%

~97%

Novel aldosterone synthase inhibitors with extended carbocyc...

[Ono, Aoi; Suzuki, Nobuko; Kamimura, Junko Synthesis, 1987 , # 8 p. 736 - 738]

Palladium-catalyzed silane/siloxane reductions in the one-po...

[Rahaim Jr., Ronald J.; Maleczka Jr., Robert E. Synthesis, 2006 , # 19 p. 3316 - 3340]

Preparation of copper nanoparticles and catalytic properties...

[Duan, Zhongyu; Ma, Guoli; Zhang, Wenjun Bulletin of the Korean Chemical Society, 2012 , vol. 33, # 12 p. 4003 - 4006]

Chemoselective hydrogenation using molecular sieves-supporte...

[Takahashi, Tohru; Yoshimura, Masatoshi; Suzuka, Hiroyasu; Maegawa, Tomohiro; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao Tetrahedron, 2012 , vol. 68, # 39 p. 8293 - 8299]

Copper/oxalohydrazide/ketone catalyzed synthesis of primary ...

[Li, Ying; Zhu, Xinhai; Meng, Fei; Wan, Yiqian Tetrahedron, 2011 , vol. 67, # 30 p. 5450 - 5454]