Oxidative Conversion of Silyl Enol Ethers to α,β-Unsaturated Ketones Employing Oxoammonium Salts

被引：48
作者：
Hayashi, Masaki [2 ]
Shibuya, Masatoshi [1 ]
Iwabuchi, Yoshiharu [1 ]
机构：
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan
[2] Daiichi Sankyo Co, Proc Technol Res Labs, Hiratsuka, Kanagawa 2540014, Japan
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 01期
基金：
日本学术振兴会;
关键词：
TERTIARY ALLYLIC ALCOHOLS; HIGHLY-ACTIVE ORGANOCATALYST; ALKYNYL GRIGNARD-REAGENTS; ARYLBORONIC ACIDS; ALPHA-OXYAMINATION; TEMPO; ALDEHYDES; EFFICIENT; REARRANGEMENT; CHEMISTRY;
D O I：
10.1021/ol2029417
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The oxidative conversion of silyl enol ethers to alpha,beta-unsaturated ketones using a less-hindered class of oxoammonium salts (AZADO(+)BF(4)(-)) is described. The reaction proceeds via the ene-like addition of oxoammonium salts to silyl enol ethers.
引用
收藏
页码：154 / 157
页数：4
相关论文
共 70 条
[1]   Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media [J].
Akagawa, Kengo ;
Fujiwara, Takuma ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
ORGANIC LETTERS, 2010, 12 (08) :1804-1807
[2]   Enantioselective organocatalysis using SOMO activation [J].
Beeson, Teresa D. ;
Mastracchio, Anthony ;
Hong, Jun-Bae ;
Ashton, Kate ;
MacMillan, David W. C. .
SCIENCE, 2007, 316 (5824) :582-585
[3]  
Bobbitt J.M., 2010, ORG REACT, V74, P103, DOI [10.1002/0471264180.or074.02, DOI 10.1002/0471264180.OR074.02]
[4]  
BOBBITT JM, 1988, HETEROCYCLES, V27, P509
[5]   Allylic oxidation: easy synthesis of alkenones from activated alkenes with TEMPO [J].
Breton, T ;
Liaigre, D ;
Belgsir, E .
TETRAHEDRON LETTERS, 2005, 46 (14) :2487-2490
[6]   Organocatalyzed α-Oxyamination of Aldehydes Using Anodic Oxidation [J].
Bui, Nhat-Nguyen ;
Ho, Xuan-Huong ;
Mho, Sun-il ;
Jang, Hye-Young .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (31) :5309-5312
[7]   Large-scale oxidations in the pharmaceutical industry [J].
Caron, Stephane ;
Dugger, Robert W. ;
Ruggeri, Sally Gut ;
Ragan, John A. ;
Ripin, David H. Brown .
CHEMICAL REVIEWS, 2006, 106 (07) :2943-2989
[8]   Efficient pyrimidine N-1-alkylation via activation of electron rich olefins with oxoanunonium salts: Synthesis of methoxy TEMPO substituted pyrimidine nucleoside analogs [J].
Church, KM ;
Holloway, LM ;
Matley, RC ;
Brower, RJ .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2004, 23 (11) :1723-1738
[9]   Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives [J].
Ciriminna, Rosaria ;
Pagliaro, Mario .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (01) :245-251
[10]  
deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153
1234567