Chiral Calcium-Catalyzed Asymmetric Epoxidation Reactions Using Hydrogen Peroxide as the Terminal Oxidant

被引：1

作者：

Yamashita, Yasuhiro ^{[1
]}

Macor, Joseph Alexander ^{[1
]}

Fushimi, Seiya ^{[1
]}

Tsubogo, Tetsu ^{[2
,3
]}

Kobayashi, Shu K ^{[1
,2
]}

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan

[2] Univ Tokyo, Grad Sch Sci, Green & Sustainable Chem Cooperat Lab, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan

[3] Tokyo Univ Sci, Fac Pharmaceut Sci, 2641 Yamazaki, Noda, Chiba 2788510, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2018年 / 66卷 / 09期

基金：

日本学术振兴会; 日本科学技术振兴机构;

关键词：

chiral calcium catalyst; asymmetric epoxidation; hydrogen peroxide; EARTH METAL-CATALYSTS; CARBON BOND FORMATION; HETEROGENEOUS CATALYSTS; CONTINUOUS-FLOW; ENANTIOSELECTIVE 1,4-ADDITION; ACID DERIVATIVES; COMPLEXES; OLEFINS;

D O I：

10.1248/cpb.c18-00485

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Asymmetric epoxidation reactions of chalcone derivatives catalyzed by chiral calcium complexes using hydrogen peroxide were developed. The epoxidation reactions proceeded smoothly to afford the desired products in good yields with good enantioselectivities. This is the first example of chiral calcium-catalyzed asymmetric epoxidation reactions using hydrogen peroxide as the terminal oxidant.

引用

页码：847 / 850

页数：4

共 30 条

[1]

[Anonymous], 1995, BASIC INORGANIC CHEM

[2] Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H2O2 and O2 [J].

Bryliakov, Konstantin P. .

CHEMICAL REVIEWS, 2017, 117 (17) :11406-11459

[3]

Greenwood NN, 2006, Chemistry of the elements, VSecond

[4] PROCEDURE FOR THE CATALYTIC ASYMMETRIC EPOXIDATION OF ALLYLIC ALCOHOLS IN THE PRESENCE OF MOLECULAR-SIEVES [J].

HANSON, RM ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1922-1925

[5] Synthesis of Glutamic Acid and Highly Functionalized Pyrrolidine Derivatives by Utilizing Tunable Calcium Catalysts for Chemoselective Asymmetric 1,4-Addition and [3+2] Cycloaddition Reactions [J].

Hut'ka, Martin ;

Tsubogo, Tetsu ;

Kobayashi, Shu .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) :1561-1569

[6] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976

[7] Calcium-catalyzed diastereo- and enantioselective 1,4-addition of glycine derivatives to α,β-unsaturated esters [J].

Kobayashi, Shu ;

Tsubogo, Tetsu ;

Saito, Susumu ;

Yamashita, Yasuhiro .

ORGANIC LETTERS, 2008, 10 (05) :807-809

[8] Flow "Fine" Synthesis: High Yielding and Selective Organic Synthesis by Flow Methods [J].

Kobayashi, Shu .

CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (04) :425-436

[9] Alkaline Earth Metal Catalysts for Asymmetric Reactions [J].

Kobayashi, Shu ;

Yamashita, Yasuhiro .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (01) :58-71

[10] Inter- and intramolecular reactions of epoxides and aziridines with π-nucleophiles [J].

Krake, Susann H. ;

Bergmeier, Stephen C. .

TETRAHEDRON, 2010, 66 (37) :7337-7360

← 1 2 3 →