Phase-Transfer-Catalyzed Enantioselective α-Hydroxylation of Acyclic and Cyclic Ketones with Oxygen

被引：78

作者：

Sim, Sui-Boon Derek ^{[1
]}

Wang, Min ^{[1
]}

Zhao, Yu ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

ACS CATALYSIS | 2015年 / 5卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

phase transfer catalysis; hydroxylation; alpha-hydroxy ketone; oxygen; cinchona alkaloid; enantioselectivity; AEROBIC ALCOHOL OXIDATIONS; MOLECULAR-OXYGEN; ORGANIC-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; OXIDASE CATALYSIS; PALLADIUM; REDUCTION; OXINDOLES; CHEMICALS;

D O I：

10.1021/acscatal.5b00583

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient and enantioselective alpha-hydroxylation of acyclic as well as cyclic ketones using molecular oxygen has been developed. This simple catalytic procedure uses a readily available phase transfer catalyst and produces a wide range of valuable tertiary a-hydroxy ketones in good to excellent enantiopurity.

引用

页码：3609 / 3612

页数：4

共 43 条

[1] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[2]

Chen B.-C., 2003, ORG REACT, V62, P1

[3] A Dinuclear Palladium Catalyst for α-Hydroxylation of Carbonyls with O2 [J].

Chuang, Gary Jing ;

Wang, Weike ;

Lee, Eunsung ;

Ritter, Tobias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) :1760-1762

[4] CHEMISTRY OF OXAZIRIDINES .14. ASYMMETRIC OXIDATION OF KETONE ENOLATES USING ENANTIOMERICALLY PURE (CAMPHORYLSULFONYL)OXAZIRIDINE [J].

DAVIS, FA ;

SHEPPARD, AC ;

CHEN, BC ;

HAQUE, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6679-6690

[5] Enantioselective PTC:: Varying the cinchona alkaloid motive [J].

Dehmlow, EV ;

Wagner, S ;

Müller, A .

TETRAHEDRON, 1999, 55 (20) :6335-6346

[6] CONCERNING THE MECHANISM OF THE REDUCTION OF HYDROPEROXIDES BY TRISUBSTITUTED PHOSPHINES AND TRISUBSTITUTED PHOSPHITES [J].

DENNEY, DB ;

GOODYEAR, WF ;

GOLDSTEIN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (06) :1393-1395

[7] ENANTIOSELECTIVE OXIDATION OF AROMATIC KETONES BY MOLECULAR-OXYGEN, CATALYZED BY CHIRAL MONOAZA-CROWN ETHERS [J].

DEVRIES, EFJ ;

PLOEG, L ;

COLAO, M ;

BRUSSEE, J ;

VANDERGEN, A .

TETRAHEDRON-ASYMMETRY, 1995, 6 (05) :1123-1132

[8] TOTAL SYNTHESIS OF THE IONOPHORE ANTIBIOTIC X-206 - STUDIES RELEVANT TO THE STEREOSELECTIVE SYNTHESIS OF THE C(17)-C(26) SYNTHON [J].

EVANS, DA ;

BENDER, SL .

TETRAHEDRON LETTERS, 1986, 27 (07) :799-802

[9] Highly enantioselective α-aminoxylation of aldehydes and ketones with a polymer-supported organocatalyst [J].

Font, Daniel ;

Bastero, Amaia ;

Sayalero, Sonia ;

Jimeno, Ciril ;

Pericas, Miquel A. .

ORGANIC LETTERS, 2007, 9 (10) :1943-1946

[10] HIGHLY DIASTEREOCONTROLLED REDUCTION OF KETONES BY MEANS OF HYDROSILANES - PRACTICAL SYNTHESIS OF OPTICALLY-ACTIVE 1,2-DIOLS AND 2-AMINO ALCOHOLS OF THREO OR ERYTHRO CONFIGURATION [J].

FUJITA, M ;

HIYAMA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) :4629-4630

← 1 2 3 4 5 →