Palladium catalyzed aerobic dehydrogenation: From alcohols to indoles and asymmetric catalysis

被引:206
作者
Stoltz, BM [1 ]
机构
[1] CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA
关键词
D O I
10.1246/cl.2004.362
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic aerobic dehydrogenation of organic substrates is going through a Renaissance. Recent advances in this area have led to the discovery of palladium-catalyzed alcohol dehydrogenations and oxidative hetero- and carbocyclizations. The development of asymmetric catalytic dehydrogenations is the latest advance in a long line of catalytic asymmetric oxidation reactions.
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页码:362 / 367
页数:6
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共 52 条
[21]  
Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4
[22]   THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].
KATSUKI, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976
[23]  
Katsuki T., 2000, CATALYTIC ASYMMETRIC, P287
[24]   Palladium(II)-catalyzed cyclization of olefinic tosylamides [J].
Larock, RC ;
Hightower, TR ;
Hasvold, LA ;
Peterson, KP .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3584-3585
[25]   A SIMPLE, EFFECTIVE, NEW, PALLADIUM-CATALYZED CONVERSION OF ENOL SILANES TO ENONES AND ENALS [J].
LAROCK, RC ;
HIGHTOWER, TR ;
KRAUS, GA ;
HAHN, P ;
ZHENG, D .
TETRAHEDRON LETTERS, 1995, 36 (14) :2423-2426
[26]   Scope of enantioselective palladium(II)-catalyzed aerobic alcohol oxidations with (-)-sparteine [J].
Mandal, SK ;
Jensen, DR ;
Pugsley, JS ;
Sigman, MS .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4600-4603
[27]   Palladium-catalyzed aerobic oxidative kinetic resolution of alcohols with an achiral exogenous base [J].
Mandal, SK ;
Sigman, MS .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) :7535-7537
[28]   Catalytic asymmetric and chemoselective aerobic oxidation: kinetic resolution of sec-alcohols [J].
Masutani, K ;
Uchida, T ;
Irie, R ;
Katsuki, T .
TETRAHEDRON LETTERS, 2000, 41 (26) :5119-5123
[29]   Mechanistic investigations of the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols using (-)-sparteine [J].
Mueller, JA ;
Sigman, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (23) :7005-7013
[30]   Dual role of (-)-sparteine in the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols [J].
Mueller, JA ;
Jensen, DR ;
Sigman, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) :8202-8203