Palladium-catalyzed oxidative kinetic resolution with ambient air as the stoichiometric oxidation gas

被引：84

作者：

Bagdanoff, JT ^{[1
]}

Stoltz, BM ^{[1
]}

机构：

[1] CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 03期

关键词：

asymmetric catalysis; hydrogen bonds; oxidation; oxygen; palladium; solvent effects;

D O I：

10.1002/anie.200352444

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Air is enough to mediate the highly enantioselective oxidation of secondary alcohols at room temperature with palladium(II) and sparteine in nonflammable solvents. Examination of the role of solvents capable of hydrogen bonding and their ability to solvate halide anions led to a novel set of conditions for the highly enantioselective oxidative kinetic resolution of secondary alcohols.

引用

页码：353 / 357

页数：5

共 19 条

[1] Palladium-catalyzed enantioselective oxidation of alcohols:: A dramatic rate acceleration by Cs2CO3/t-BuOH [J].

Bagdanoff, JT ;

Ferreira, EM ;

Stoltz, BM .

ORGANIC LETTERS, 2003, 5 (06) :835-837

[2] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

[3]

FABER K, 1997, BIOTRANSFORMATIONS O, P201

[4] Catalytic C-H bond functionalization with palladium(II):: Aerobic oxidative annulations of indoles [J].

Ferreira, EM ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9578-9579

[5] The palladiuim-catalyzed oxidative kinetic resolution of secondary alcohols with molecular oxygen [J].

Ferreira, EM ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7725-7726

[6] The solubility of oxygen in various organic solvents [J].

Fischer, F ;

Pfleiderer, G .

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1922, 124 (01) :61-69

[7]

FLICK EW, 1985, IND SOLVENT HDB, P637

[8]

Hallman K, 2001, ADV SYNTH CATAL, V343, P260, DOI 10.1002/1615-4169(20010330)343:3<260::AID-ADSC260>3.3.CO

[9]

2-#

[10]

JACKOVAC IJ, 1982, J AM CHEM SOC, V104, P4659

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