NHC Catalyzed Oxidations of Aldehydes to Esters: Chemoselective Acylation of Alcohols in Presence of Amines

被引:341
作者
De Sarkar, Suman [1 ]
Grimme, Stefan [1 ]
Studer, Armido [1 ]
机构
[1] Univ Munster, Organisch Chem Inst, NRW Grad Sch Chem, D-48149 Munster, Germany
关键词
STEREOSELECTIVE-SYNTHESIS; ACTIVATED CARBOXYLATES; SELECTIVE ACYLATION; ESTERIFICATION; GENERATION; CONVERSION; AMIDATION; PEPTIDES;
D O I
10.1021/ja910540j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Not just one but two carbenes of the same structure act cooperatively in oxidative acylations of alcohols with aldehydes by using a readily available cheap organic oxidant. Alcohols are selectively acylated in the presence of amines by cooperative carbene catalysis. Quantum chemical calculations Support the suggested mechanism.
引用
收藏
页码:1190 / +
页数:4
相关论文
共 29 条
[1]   Conversion of α,β-unsaturated aldehydes into saturated esters:: An umpolung reaction catalyzed by nucleophilic carbenes [J].
Chan, A ;
Scheidt, KA .
ORGANIC LETTERS, 2005, 7 (05) :905-908
[2]   Catalytic generation of activated carboxylates:: Direct, stereoselective synthesis of β-hydroxyesters from epoxyaldehydes [J].
Chow, KYK ;
Bode, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8126-8127
[3]   One-pot oxidative esterification and amidation of aldehydes [J].
Ekoue-Kovi, Kekeli ;
Wolf, Christian .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (21) :6302-6315
[4]   Organocatalysis by N-heterocyclic, carbenes [J].
Enders, Dieter ;
Niemeier, Oliver ;
Henseler, Alexander .
CHEMICAL REVIEWS, 2007, 107 (12) :5606-5655
[5]   SELECTIVE ACYLATION OF PEPTIDES CATALYZED BY LIPASES IN ORGANIC-SOLVENTS [J].
GARDOSSI, L ;
BIANCHI, D ;
KLIBANOV, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6328-6329
[6]  
Greene T.W., 1991, PROTECTIVE GROUPS OR, V2nd
[7]   Semiempirical GGA-type density functional constructed with a long-range dispersion correction [J].
Grimme, Stefan .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2006, 27 (15) :1787-1799
[8]   Biomimetic Carbene-Catalyzed Oxidations of Aldehydes Using TEMPO [J].
Guin, Joyram ;
De Sarkar, Suman ;
Grimme, Stefan ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (45) :8727-8730
[9]   Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides [J].
Humphrey, JM ;
Chamberlin, AR .
CHEMICAL REVIEWS, 1997, 97 (06) :2243-2266
[10]  
JABLOSKI M, 2009, PHYS CHEM CHEM PHYS, V1, P5711