Direct substitution of the hydroxy group with highly functionalized nitrogen nucleophiles catalyzed by Au(III)

被引：49
作者：
Ohshima, Takashi [1 ,2 ]
Nakahara, Yasuhito [3 ,4 ]
Ipposhi, Junji [3 ,4 ]
Miyamoto, Yoshiki [3 ,4 ]
Mashima, Kazushi [3 ,4 ]
机构：
[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 812, Japan
[2] JST, CREST, Fukuoka, Japan
[3] Osaka Univ, Dept Chem, Grad Sch Engn Sci, Osaka, Japan
[4] JST, CREST, Osaka, Japan
来源：
CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 29期
关键词：
DIRECT AMINATION; ALLYLIC ALCOHOLS; PROPARGYLIC ALCOHOLS; BENZYL ALCOHOLS; DIASTEREOSELECTIVE SYNTHESIS; BORROWING HYDROGEN; GOLD CATALYSIS; N-ALKYLATION; SULFONAMIDES; AMIDATION;
D O I：
10.1039/c1cc12760h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A direct catalytic substitution of various allylic and benzylic alcohols with synthetically useful, but acid-sensitive Boc, Bus, and Dios protected amine nucleophiles, which have not been well utilized for Lewis acid catalysis, with various functionalities (OTBS, OTHP, etc.) was efficiently catalyzed by 1 mol% of Au(III) under mild conditions.
引用
收藏
页码：8322 / 8324
页数：3
相关论文
共 64 条
[1]   Fe(II)-catalyzed N-alkylation of sulfonamides with benzylic alcohols [J].
Cui, Xinjiang ;
Shi, Feng ;
Zhang, Yan ;
Deng, Youquan .
TETRAHEDRON LETTERS, 2010, 51 (15) :2048-2051
[2]   A Dual Gold-Iron Catalysis for a One-Pot Synthesis of 2,3-Dihydroisoxazoles from Propargylic Alcohols and N-Protected Hydroxylamines [J].
Debleds, Olivier ;
Dal Zotto, Christophe ;
Vrancken, Emmanuel ;
Campagne, Jean-Marc ;
Retailleau, Pascal .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) :1991-1998
[3]   Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols: Sulfamic acid as amonia equivalent [J].
Defieber, Christian ;
Ariger, Martin A. ;
Moriel, Patricia ;
Carreira, Erick M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (17) :3139-3143
[4]   Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis [J].
Dobereiner, Graham E. ;
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2010, 110 (02) :681-703
[5]   Intra- and intermolecular reactions of indoles with alkynes catalyzed by gold [J].
Ferrer, Catalina ;
Amijs, Catelijne H. M. ;
Echavarren, Antonio M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (05) :1358-1373
[6]   Gold (III)-catalyzed direct nucleophilic substitution of propargylic alcohols [J].
Georgy, Marie ;
Boucard, Valerie ;
Debleds, Olivier ;
Dal Zotto, Christophe ;
Campagne, Jean-Marc .
TETRAHEDRON, 2009, 65 (09) :1758-1766
[7]   tert-butylsulfonamide.: A new nitrogen source for catalytic aminohydroxylation and aziridination of olefins [J].
Gontcharov, AV ;
Liu, H ;
Sharpless, KB .
ORGANIC LETTERS, 1999, 1 (05) :783-786
[8]   Copper(I)-fesulphos Lewis acid catalysts for enantioselective Mannich-type reaction of N-sulfonyl imines [J].
Gonzalez, Alvaro Salvador ;
Arrayas, Ramon Gomez ;
Carretero, Juan C. .
ORGANIC LETTERS, 2006, 8 (14) :2977-2980
[9]  
GREGORY M, 2005, J AM CHEM SOC, V127, P14180
[10]   FeCl3-Catalyzed Highly Diastereoselective Synthesis of Substituted Piperidines and Tetrahydropyrans [J].
Guerinot, Amandine ;
Serra-Muns, Anna ;
Gnamm, Christian ;
Bensoussan, Charlelie ;
Reymond, Sebastien ;
Cossy, Janine .
ORGANIC LETTERS, 2010, 12 (08) :1808-1811
1234567