Ir-Catalyzed α-Alkylation of Methyl Ketones with Primary Carbohydrate Alcohols

被引:4
作者
Tsuge, Kouki [1 ]
Kubota, Shunnichi [1 ]
Sakamoto, Kana [1 ]
Kitayama, Kenji [2 ]
Nishimura, Takahiro [1 ]
机构
[1] Osaka Metropolitan Univ, Grad Sch Sci, Dept Chem, Sumiyoshi, Osaka 5588585, Japan
[2] Daicel Corp, Grand Front Osaka Tower-B, 3-1,Ofuka Cho,Kita Ku, Osaka 5300011, Japan
关键词
Iridium; Sugars; Methyl Ketones; Alkylation; Hydrogen Transfer; BORROWING HYDROGEN; AMINES;
D O I
10.1002/adsc.202300124
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Iridium-catalyzed alpha-alkylation of methyl ketones with primary carbohydrate alcohols proceeded via borrowing hydrogen strategy. Protected sugar derivatives having one free primary hydroxyl group reacted with methyl ketones to give the alpha-alkylation products or alkylated 4,5-unsaturated sugars along with the elimination of an alkoxy group.
引用
收藏
页码:971 / 975
页数:5
相关论文
共 39 条
[1]  
[Anonymous], 2016, ANGEW CHEM INT EDIT, V55, P14967
[2]  
[Anonymous], 2015, ANGEW CHEM INT EDIT, V54, P14483
[3]   Phosphine-Free NNN-Manganese Complex Catalyzed α-Alkylation of Ketones with Primary Alcohols and Friedlander Quinoline Synthesis [J].
Barman, Milan K. ;
Jana, Akash ;
Maji, Biplab .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (17) :3233-3238
[4]   Iridium catalysed chemoselective alkylation of 2′-aminoacetophenone with primary benzyl type alcohols under microwave conditions [J].
Bhat, Shailen ;
Sridharan, Visuvanathar .
CHEMICAL COMMUNICATIONS, 2012, 48 (39) :4701-4703
[5]   NNN Pincer Ru(II)-Complex-Catalyzed α-Alkylation of Ketones with Alcohols [J].
Cao, Xiao-Niu ;
Wan, Xiao-Min ;
Yang, Fa-Liu ;
Li, Ke ;
Hao, Xin-Qi ;
Shao, Tian ;
Zhu, Xinju ;
Song, Mao-Ping .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07) :3657-3668
[6]   Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols [J].
Chakraborty, Subrata ;
Daw, Prosenjit ;
Ben David, Yehoshoa ;
Milstein, David .
ACS CATALYSIS, 2018, 8 (11) :10300-10305
[7]   Ruthenium-catalyzed regioselective α-alkylation of ketones with primary alcohols [J].
Cho, CS ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
TETRAHEDRON LETTERS, 2002, 43 (44) :7987-7989
[8]   Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis [J].
Corma, Avelino ;
Navas, Javier ;
Sabater, Maria J. .
CHEMICAL REVIEWS, 2018, 118 (04) :1410-1459
[9]   Iridium-catalysed condensation of alcohols and amines as a method for aminosugar synthesis [J].
Cumpstey, Ian ;
Agrawal, Santosh ;
Borbas, K. Eszter ;
Martin-Matute, Belen .
CHEMICAL COMMUNICATIONS, 2011, 47 (27) :7827-7829
[10]   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