Iron(III)-salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles

被引：103

作者：

Gu, Xin ^{[1
]}

Zhang, Yan ^{[1
]}

Xu, Zhen-Jiang ^{[1
]}

Che, Chi-Ming ^{[1
,2
,3
]}

机构：

[1] Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai, Peoples R China

[2] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China

[3] Univ Hong Kong, State Key Lab Synthet Chem, Hong Kong, Hong Kong, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 58期

关键词：

C-H ACTIVATION; CARBONYL-COMPOUNDS; ALPHA-HYDROXYLATION; CIS-DIHYDROXYLATION; MECHANISTIC ASPECTS; HYDROGEN-PEROXIDE; ORGANIC-SYNTHESIS; DFT CALCULATIONS; IRON COMPLEXES; BOND AMINATION;

D O I：

10.1039/c4cc01631a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral iron(III)-salan complexes catalysed highly enantioselective alpha-fluorination and alpha-hydroxylation of beta-keto esters and N-Boc oxindoles to give the corresponding products in high yields and good-to-excellent ee values under mild reaction conditions.

引用

页码：7870 / 7873

页数：4

共 66 条

[41] Nonheme Iron-Mediated Amination of C(sp3)-H Bonds. Quinquepyridine-Supported Iron-Imide/Nitrene Intermediates by Experimental Studies and DFT Calculations [J].

Liu, Yungen ;

Guan, Xiangguo ;

Wong, Ella Lai-Ming ;

Liu, Peng ;

Huang, Jie-Sheng ;

Che, Chi-Ming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (19) :7194-7204

[42] [FeIII(F20-tpp)Cl] Is an Effective Catalyst for Nitrene Transfer Reactions and Amination of Saturated Hydrocarbons with Sulfonyl and Aryl Azides as Nitrogen Source under Thermal and Microwave-Assisted Conditions [J].

Liu, Yungen ;

Che, Chi-Ming .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (34) :10494-10501

[43] Chiral Bronsted Acid-Catalyzed Enantioselective α-Hydroxylation of β-Dicarbonyl Compounds [J].

Lu, Min ;

Zhu, Di ;

Lu, Yunpeng ;

Zeng, Xiaofei ;

Tan, Bin ;

Xu, Zhenjiang ;

Zhong, Guofu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (13) :4562-+

[44] Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions [J].

Lyons, Thomas W. ;

Sanford, Melanie S. .

CHEMICAL REVIEWS, 2010, 110 (02) :1147-1169

[45] Enantioselective formation of stereogenic carbon-fluorine centers by a simple catalytic method [J].

Marigo, M ;

Fielenbach, DI ;

Braunton, A ;

Kjoersgaard, A ;

Jorgensen, KA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (24) :3703-3706

[46] Dioxidomolybdenum(VI) Complexes Containing Ligands with the Bipyrrolidine Backbone as Efficient Catalysts for Olefin Epoxidation [J].

Mayilmurugan, Ramasamy ;

Traar, Pedro ;

Schachner, Joerg A. ;

Volpe, Manuel ;

Moesch-Zanetti, Nadia C. .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2013, 2013 (21) :3664-3670

[47] C-H Activation for the Construction of C-B Bonds [J].

Mkhalid, Ibraheem A. I. ;

Barnard, Jonathan H. ;

Marder, Todd B. ;

Murphy, Jaclyn M. ;

Hartwig, John F. .

CHEMICAL REVIEWS, 2010, 110 (02) :890-931

[48] Chiral iron complex catalyzed enantioselective oxidation of racemic benzoins [J].

Muthupandi, Pandi ;

Alamsetti, Santosh Kumar ;

Sekar, Govindasamy .

CHEMICAL COMMUNICATIONS, 2009, (22) :3288-3290

[49]

Nicolas L., 2006, SYNTHESIS-STUTTGART, P1701

[50] Highly enantioselective Mukaiyama aldol reaction in aqueous conditions using a chiral iron(II) bipyridine catalyst [J].

Ollevier, Thierry ;

Plancq, Baptiste .

CHEMICAL COMMUNICATIONS, 2012, 48 (17) :2289-2291

← 1 2 3 4 5 6 7 →