Metal-Catalyzed One-Step Synthesis: Towards Direct Alternatives to Multistep Heterocycle and Amino Acid Derivative Formation

被引:110
作者
Arndtsen, Bruce A. [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
carbonylation; green chemistry; heterocycles; metal catalysis; multicomponent reactions; MULTICOMPONENT-COUPLING REACTIONS; CARBONYLATIVE RING EXPANSION; CHROMIUM CARBENE COMPLEXES; ALPHA-SUBSTITUTED AMIDES; PAUSON-KHAND REACTION; ONE-POT; CARBON-MONOXIDE; BETA-LACTAMS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS;
D O I
10.1002/chem.200800767
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The growing understanding of transition-metal catalysis has provided the opportunity to design reactions that convert simple. readily available building blocks in one step into an array of biologically relevant products. Described herein is the application of this approach to the construction of various biologically relevant products. including pyrroles, imidazoles, beta-lactams. oxazoles, alpha-amino acids. propargyl amides, functionalized pyridines, and others. These catalytic reactions rely upon several synthetic operations occurring in sequence, ill which the reactivity of transition-metal complexes both activates basic building blocks towards reaction, and controls how multiple versions of these substrates come together. Overall. this allows the synthesis of each these products in one step. ill high yield, with minimal waste, and with straightforward access to product diversity.
引用
收藏
页码:302 / 313
页数:12
相关论文
共 151 条
[1]   Palladium-assisted multicomponent synthesis of 2-aryl-4-aminoquinolines and 2-aryl-4-amino[1,8]naphthyridines [J].
Abbiati, G ;
Arcadi, A ;
Canevari, V ;
Capezzuto, L ;
Rossi, E .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6454-6460
[2]   General and efficient indole syntheses based on catalytic amination reactions [J].
Ackermann, L .
ORGANIC LETTERS, 2005, 7 (03) :439-442
[3]   One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling [J].
Ahmed, MSM ;
Kobayashi, K ;
Mori, A .
ORGANIC LETTERS, 2005, 7 (20) :4487-4489
[4]   Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines [J].
Akullian, LC ;
Snapper, ML ;
Hoveyda, AH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4244-4247
[5]  
AKULLIAN LC, 2003, ANGEW CHEM, V115, P4376, DOI DOI 10.1002/ANGE.200352081
[6]   NOVEL SYNTHESES OF MESOIONIC COMPOUNDS AND ALPHA-AMINO-ACID DERIVATIVES FROM ACYLTETRACARBONYLFERRATES [J].
ALPER, H ;
TANAKA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (15) :4245-4249
[7]  
Anastas P., 1998, GREEN CHEM THEORY PR
[8]   Stereochemical control of the Passerini reaction [J].
Andreana, PR ;
Liu, CC ;
Schreiber, SL .
ORGANIC LETTERS, 2004, 6 (23) :4231-4233
[9]  
[Anonymous], ANGEW CHEM
[10]  
[Anonymous], 2006, ANGEW CHEM