Article

Enantioselective Arylation of 2-Methylacetoacetates Catalyzed by CuI/trans-4-Hydroxy-L-proline at Low Reaction Temperatures.

Department of Chemistry, Fudan University, Shanghai 200433, China.
Journal of the American Chemical Society (Impact Factor: 11.44). 04/2007; 128(50):16050-1. DOI: 10.1021/ja066991j
Source: PubMed

ABSTRACT CuI/trans-4-hydroxy-l-proline-catalyzed coupling reaction of 2-iodotrifluoroacetanilides with 2-methylacetoacetates took place at -45 degrees C to create alpha-aryl all-carbon quaternary centers enantioselectively. Up to 93% ee was achieved when tert-butyl ester was used. The combination of ligand, ortho substituent (participation of NHCOCF3), and solvent effects was shown to account for these unprecedentedly mild reaction conditions.

0 Bookmarks
 · 
58 Views
  • [Show abstract] [Hide abstract]
    ABSTRACT: A convenient CuI/L-proline-catalyzed, two-step one-pot method has been developed for the preparation of indolo[1,2-a]quinazoline derivatives using a sequential Ullmann-type C-C and C-N coupling. This protocol provides an operationally simple and rapid strategy for preparing indolo[1,2-a]quinazoline derivatives and displays good functional group tolerance. All the starting materials are commercial available or can be easily prepared.
    Beilstein Journal of Organic Chemistry 01/2014; 10:2441-7. DOI:10.3762/bjoc.10.254 · 2.80 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Quaternary carbon stereocentres-carbon atoms to which four distinct carbon substituents are attached-are common features of molecules found in nature. However, before recent advances in chemical catalysis, there were few methods of constructing single stereoisomers of this important structural motif. Here we discuss the many catalytic enantioselective reactions developed during the past decade for the synthesis of single stereoisomers of such organic molecules. This progress now makes it possible to incorporate quaternary stereocentres selectively in many organic molecules that are useful in medicine, agriculture and potentially other areas such as flavouring, fragrances and materials.
    Nature 12/2014; 516(7530):181-91. DOI:10.1038/nature14007 · 42.35 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: The chemistry of natural products has emerged as an extremely important area of contemporary research owing to their profound biological activities, complex molecular architecture with challenging stereochemistry and potential for use as medicine. Searches for efficient synthetic procedures for natural products, drugs, and materials with economical and ecological advantages are important areas of current research interest. This article describes the isolation, bioactivity and synthesis of several natural products and drugs by employing coinage metal-catalyzed/mediated reaction/strategy either in a sequential or a domino fashion. We have made an attempt to summarize the progress made in the area from 2008 onwards.
    RSC Advances 01/2014; 4(16):8085. DOI:10.1039/c3ra44336a · 3.71 Impact Factor