Recent developments in the use of catalytic asymmetric ammonium enolates in chemical synthesis

被引:258
作者
Gaunt, Matthew J. [1 ]
Johansson, Carin C. C. [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
关键词
D O I
10.1021/cr0683764
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A review on the recent development of methods that makes use of chiral tertiary amine catalysts as a source to generate asymmetric ammonium enolates is presented. The types of ammonium enolates were identified. A discussion was made on the catalytic asymmetric C1 ammonium enolates. Both the type B and C of ammonium enolates were described. The type B had the catalytic asymmetric ammonium ylides while the type C had the catalytic asymmetric C3 substituted ammonium enolates.
引用
收藏
页码:5596 / 5605
页数:10
相关论文
共 96 条
[1]   Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].
Aggarwal, VK ;
Winn, CL .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620
[2]   Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis-Hillman reaction [J].
Balan, D ;
Adolfsson, H .
TETRAHEDRON LETTERS, 2003, 44 (12) :2521-2524
[3]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[4]   Catalytic, enantioselective [4+2]-cycloadditions of ketene enolates and o-quinones:: Efficient entry to chiral, α-oxygenated carboxylic acid derivatives [J].
Bekele, T ;
Shah, MH ;
Wolfer, J ;
Abraham, CJ ;
Weatherwax, A ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :1810-1811
[5]  
BERKESSEL A, 2005, ASYMMETRIC ORGNOCATA
[6]  
BHATTACHARJEE SS, 1982, SYNTHESIS-STUTTGART, P301
[7]   UBER DIE UMSETZUNG VON CARBONYLVERBINDUNGEN MIT SAURECHLORIDEN IN GEGENWART TERTIARER AMINE .2. OPTISCH AKTIVE BETA-LACTONE [J].
BORRMANN, D ;
WEGLER, R .
CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (05) :1575-&
[8]   An intramolecular organocatalytic cyclopropanation reaction [J].
Bremeyer, N ;
Smith, SC ;
Ley, SV ;
Gaunt, MJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (20) :2681-2684
[9]   Catalytic, asymmetric preparation of ketene dimers from acid chlorides [J].
Calter, MA ;
Orr, RK ;
Song, W .
ORGANIC LETTERS, 2003, 5 (24) :4745-4748
[10]   First total synthesis of a natural product containing a chiral, β-diketone:: Synthesis and stereochemical reassignment of siphonarienedione and siphonarienolone [J].
Calter, MA ;
Liao, WS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13127-13129