A Sc(OTf)3 catalyzed Mukaiyama-Mannich reaction of difluoroenoxysilanes with unactivated ketimines

被引：23

作者：

Hu, Xiao-Si ^{[1
]}

Ding, Pei-Gang ^{[1
]}

Yu, Jin-Sheng ^{[1
]}

Zhou, Jian ^{[1
,2
]}

机构：

[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Shanghai 200062, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 14期

关键词：

DIFLUORO-BETA-LACTAMS; ENOL SILYL ETHERS; ORGANOFLUORINE-ORGANOSILICON CHEMISTRY; ENANTIOSELECTIVE STRECKER REACTION; ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; HIGHLY EFFICIENT; ALDOL REACTION; REFORMATSKY REACTION; ALLYLATION REACTION;

D O I：

10.1039/c9qo00577c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Mukaiyama-Mannich reaction of difluoroenoxysilanes with unactivated ketimines enabled by 5 mol% of Sc(OTf)(3) is reported here. This protocol provides expedient access to a series of alpha,alpha-difluoro-beta-amino ketones possessing a tetrasubstituted carbon center in moderate to high yields (up to 89% yield). Moreover, the Mannich adducts could be easily converted into diversified gem-difluorinated compounds.

引用

页码：2500 / 2505

页数：6

共 112 条

[1] Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].

Alonso, Concepcion ;

Martinez de Marigorta, Eduardo ;

Rubiales, Gloria ;

Palacios, Francisco .

CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935

[2]

Baes C. F., 1976, HYDROLYSIS CATIONS

[3] Enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers [J].

Belanger, Etienne ;

Cantin, Katy ;

Messe, Olivier ;

Tremblay, Melanie ;

Paquin, Jean-Francois .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1034-1035

[4] Design, Synthesis, and Applications of Potential Substitutes of t-BuPhosphinooxazoline in Pd-Catalyzed Asymmetric Transformations and Their Use for the Improvement of the Enantioselectivity in the Pd-Catalyzed Allylation Reaction of Fluorinated Allyl Enol Carbonates [J].

Belanger, Etienne ;

Pouliot, Marie-France ;

Courtemanche, Marc-Andre ;

Paquin, Jean-Francois .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) :317-331

[5]

Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine

[6] Synthesis of α,α-difluoro-β-amino esters or gem-difluoro-β-lactams as potential metallocarboxypeptidase inhibitors [J].

Boyer, Nicolas ;

Gloanec, Philippe ;

De Nanteuil, Guillaume ;

Jubault, Philippe ;

Quirion, Jean-Charles .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (25) :4277-4295

[7] Chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams from ethylbromodifluoroacetate and imines during Reformatsky reaction [J].

Boyer, Nicolas ;

Gloanec, Philippe ;

De Nanteuil, Guillaume ;

Jubault, Philippe ;

Quirion, Jean-Charles .

TETRAHEDRON, 2007, 63 (50) :12352-12366

[8]

Burgess J., 1978, METAL IONS SOLUTION

[9] Metal-Mediated Reformatsky Reaction of Bromodifluoromethyl Ketone and Imine [J].

Cao, Chun-Ru ;

Jiang, Min ;

Liu, Jin-Tao .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (05) :1144-1151

[10] Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles [J].

Cao, Zhong-Yan ;

Zhou, Feng ;

Zhou, Jian .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (06) :1443-1454

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