Palladium-Catalyzed Chemo- and Enantioselective C-O Bond Cleavage of α-Acyloxy Ketones by Hydrogenolysis

被引：38

作者：

Chen, Jianzhong ^{[1
]}

Zhang, Zhenfeng ^{[2
]}

Liu, Delong ^{[2
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Sch Pharm, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 29期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

cleavage reactions; hydrogenolysis; ketones; kinetic resolution; palladium; ASYMMETRIC HYDROGENATION; PROTECTING GROUPS; PHENACYL ESTERS; DERIVATIVES; EFFICIENT; CYCLIZATION; PHOTOLYSIS; RESOLUTION; COMPLEXES; ALDEHYDES;

D O I：

10.1002/anie.201603590

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chemoselective C-O bond cleavage of the ester alkyl side-chain of alpha-acyloxy ketones was realized for the first time by a highly efficient palladium-catalyzed hydrogenolysis (S/C= 6000, the highest catalytic efficiency by far). Furthermore, a kinetic resolution of alpha-acyloxy ketones was first developed by enantioselective hydrogenolysis with good yields and up to 99% ee.

引用

页码：8444 / 8447

页数：4

共 36 条

[1] Readily Available Ruthenium Complex for Efficient Dynamic Kinetic Resolution of Aromatic α-Hydroxy Ketones [J].

Agrawal, Santosh ;

Martinez-Castro, Elisa ;

Marcos, Rocio ;

Martin-Matute, Belen .

ORGANIC LETTERS, 2014, 16 (08) :2256-2259

[2] Enantioselective Acylation of 1,2-and 1,3-Diols Catalyzed by Aminophosphinite Derivatives of (1S,2R)-1-Amino-2-indanol [J].

Aida, Hiroyuki ;

Mori, Kouhei ;

Yamaguchi, Yasuyuki ;

Mizuta, Shinya ;

Moriyama, Tomomi ;

Yamamoto, Iwao ;

Fujimoto, Tetsuya .

ORGANIC LETTERS, 2012, 14 (03) :812-815

[3]

[Anonymous], 2015, ANGEW CHEM, V127, P6704

[4] Synthesis of Enantiopure 1,4-Dioxanes, Morpholines, and Piperazines from the Reaction of Chiral 1,2-Diols, Amino Alcohols, and Diamines with Vinyl Selenones [J].

Bagnoli, Luana ;

Scarponi, Catalina ;

Rossi, Maria Giovanna ;

Testaferri, Lorenzo ;

Tiecco, Marcello .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) :993-999

[5] Protecting groups that can be removed through photochemical electron transfer: Mechanistic and product studies on photosensitized release of carboxylates from phenacyl esters [J].

Banerjee, A ;

Falvey, DE .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6245-6251

[6] Direct photolysis of phenacyl protecting groups studied by laser flash photolysis: An excited state hydrogen atom abstraction pathway leads to formation of carboxylic acids and acetophenone [J].

Banerjee, A ;

Falvey, DE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (12) :2965-2966

[7] Methylsulfinyl (Dimsyl) Anion as Umpolung Catalyst for the Chemoselective Cross-Benzoin Reaction of α-Diketones with Aldehydes [J].

Bortolini, Olga ;

Fantin, Giancarlo ;

Ferretti, Valeria ;

Fogagnolo, Marco ;

Giovannini, Pier Paolo ;

Massi, Alessandro ;

Pacifico, Salvatore ;

Ragno, Daniele .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (16) :3244-3252

[8]

Chen J., 2013, ANGEW CHEM, V125, P11846

[9] Palladium-Catalyzed Asymmetric Hydrogenation of α-Acyloxy-1-arylethanones [J].

Chen, Jianzhong ;

Liu, Delong ;

Butt, Nicholas ;

Li, Chao ;

Fan, Dongyang ;

Liu, Yangang ;

Zhang, Wanbin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) :11632-11636

[10] Metal-Free Reductive Cleavage of C-O σ-bonds in Acyloin Derivatives by an Organic Neutral Super-Electron-Donor [J].

Cutulic, Sylvain P. Y. ;

Findlay, Neil J. ;

Zhou, Sheng-Ze ;

Chrystal, Ewan J. T. ;

Murphy, John A. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) :8713-8718

← 1 2 3 4 →