887917-86-4Relevant academic research and scientific papers
Catalytic asymmetric Exo-selective [C+NC+CC] reaction
Joseph, Ryan,Murray, Charles,Garner, Philip
, p. 1550 - 1553 (2014/04/17)
A catalytic asymmetric version of the exo-selective [C+NC+CC] reaction is reported. This multicomponent reaction utilizes a readily prepared achiral glycyl sultam as the "NC" component and commercially available catalyst components. The method can be applied to a variety of aldehydes ("C" component) and activated alkenes ("CC" component) to provide substituted pyrrolidines in good yields and high enantioselectivities. Of particular note is the ability to employ labile enolizable aldehydes (e.g., acetaldehyde and propionaldehyde) in this reaction.
Metal amides as the simplest acid/base catalysts for stereoselective carbon-carbon bond-forming reactions
Yamashita, Yasuhiro,Kobayashi, Shu
, p. 9420 - 9427 (2013/07/26)
In this paper, new possibilities for metal amides are described. Although typical metal amides are recognized as strong stoichiometric bases for deprotonation of inert or less acidic hydrogen atoms, transition-metal amides, namely silver and copper amides
Cu-catalyzed asymmetric [3+2] cycloaddition of α-iminoamides with activated olefins
Gonzalez-Esguevillas, Maria,Adrio, Javier,Carretero, Juan C.
, p. 2149 - 2151 (2012/03/11)
A variety of 2-amido pyrrolidines, including Weinreb-type amides, have been prepared with very high exo diastereoselectivity and enantioselectivitiy in the reaction of α-iminoamides with activated alkenes catalyzed by Cu I-Segphos ligands.
Chiral silver amide catalyst for the [3+2] cycloaddition of α-amino esters to olefins
Yamashita, Yasuhiro,Imaizumi, Takaki,Kobayashi, Sha
supporting information; experimental part, p. 4893 - 4896 (2011/06/26)
Silver lining: Highly exo-selective asymmetric [3+2]cycloaddition of α-amino ester Schiff bases with activated olefins proceeds in the presence of AgHMDS/1. The α-amino ester Schiff bases including those derived from aliphatic imines successfully reacted
Chiral silver amides as effective catalysts for enantioselective [3+2] cycloaddition reactions
Yamashita, Yasuhiro,Imaizumi, Takaki,Guo, Xun-Xiang,Kobayashi, Shu
supporting information; experimental part, p. 2550 - 2559 (2012/06/18)
Asymmetric [3+2] cycloaddition of α-aminoester Schiff bases with substituted olefins is one of the most efficient methods for the preparation of chiral pyrrolidine derivatives in optically pure form. In spite of its potential utility, applicable substrate
Highly enantioselective asymmetric 1,3-dipolar cycloaddition of azomethine ylide catalyzed by a copper(l)/clickferrophos complex
Fukuzawa, Shin-Ichi,Oki, Hiroshi
supporting information; experimental part, p. 1747 - 1750 (2009/04/12)
A copper(l)/ClickFerrophos complex catalyzed the asymmetric 1.3-dipolar cycloaddition reaction of methyl N-benzyhdeneglycmate (the source of azomethlne ylides) with vinyl sulfone to give the exo-2,4,5-trisubstituted pyrrolidine in good yield with high enantioselectivity (99% ee). The complex also effectively catalyzed reactions of other dipolarophiles such as acrylates. maleate, and maleimides to give the exo-2,4.5-, and 2,3,4,5-substituted pyrrolidine derivatives with high diastereo- and enantioselectivities. American Chemical society.
Copper(I)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones
Llamas, Tomas,Arrayas, Ramon Gomez,Carretero, Juan Carlos
, p. 950 - 956 (2008/01/06)
The combination of copper(I)-Taniaphos (5 mol%) is an efficient Lewis acid catalyst for the promotion of the asymmetric 1,3-dipolar cycloaddition of azomethine ylides to aryl vinyl sulfones, providing 3-sulfonylpyrrolidines in good yields and with nearly
Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones
Llamas, Tomas,Arrayas, Ramon Gomez,Carretero, Juan C.
, p. 1795 - 1798 (2007/10/03)
A general protocol for the enantioselective catalytic 1,3-dipolar cycloaddition of azomethine ylides with aryl vinyl sulfones is described. Nearly complete exo selectivity and enantioselectivities up to 85% ee are attained with Cu(CH3CN)4
