Direct carbon–carbon bond formation via reductive soft enolization: a syn-selective Mannich addition of α-iodo thioesters

2016 ◽  
Vol 14 (33) ◽  
pp. 7864-7868 ◽  
Author(s):  
Ngoc Truong ◽  
Scott J. Sauer ◽  
Cyndie Seraphin-Hatcher ◽  
Don M. Coltart
Keyword(s):  
Carboxylic Acid ◽  
Bond Formation ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Acid Moiety ◽  
Active Compounds ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Soft Enolization ◽  
Amino Carboxylic Acid

The β-amino carboxylic acid moiety is a key feature of numerous important biologically active compounds.

ChemInform Abstract: Direct Carbon-Carbon Bond Formation via Soft Enolization: Aldol Addition of α-Halogenated Thioesters.

ChemInform ◽  
2011 ◽  
Vol 42 (18) ◽  
pp. no-no
Author(s):  
Julianne M. Yost ◽  
Rachel J. Alfie ◽  
Emily M. Tarsis ◽  
Insun Chong ◽  
Don M. Coltart
Keyword(s):  
Bond Formation ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Soft Enolization ◽  
Aldol Addition

scholarly journals Direct carbon–carbon bond formation via soft enolization: aldol addition of α-halogenated thioesters

2011 ◽  
Vol 47 (1) ◽  
pp. 571-572 ◽  
Author(s):  
Julianne M. Yost ◽  
Rachel J. Alfie ◽  
Emily M. Tarsis ◽  
Insun Chong ◽  
Don M. Coltart
Keyword(s):  
Bond Formation ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Soft Enolization ◽  
Aldol Addition

Direct Carbon-Carbon Bond Formation via Soft Enolization of Thioesters: An Operationally Simple Mannich Addition Reaction

Synthesis ◽  
2008 ◽  
Vol 2009 (01) ◽  
pp. 56-58 ◽  
Author(s):  
Don M. Coltart ◽  
Julianne Yost ◽  
Michelle Garnsey ◽  
Mark Kohler
Keyword(s):  
Addition Reaction ◽  
Bond Formation ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Soft Enolization

scholarly journals Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds

2011 ◽  
Vol 7 ◽  
pp. 59-74 ◽  
Author(s):  
Carolin Fischer ◽  
Burkhard Koenig
Keyword(s):  
Large Scale ◽  
Standard Procedure ◽  
Bond Formation ◽  
Reaction Times ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
High Yield ◽  
Active Compounds ◽  
Advantages And Disadvantages ◽  
Ring Structures

N-Arylated aliphatic and aromatic amines are important substituents in many biologically active compounds. In the last few years, transition-metal-mediated N-aryl bond formation has become a standard procedure for the introduction of amines into aromatic systems. While N-arylation of simple aromatic halides by simple amines works with many of the described methods in high yield, the reactions may require detailed optimization if applied to the synthesis of complex molecules with additional functional groups, such as natural products or drugs. We discuss and compare in this review the three main N-arylation methods in their application to the synthesis of biologically active compounds: Palladium-catalysed Buchwald–Hartwig-type reactions, copper-mediated Ullmann-type and Chan–Lam-type N-arylation reactions. The discussed examples show that palladium-catalysed reactions are favoured for large-scale applications and tolerate sterically demanding substituents on the coupling partners better than Chan–Lam reactions. Chan–Lam N-arylations are particularly mild and do not require additional ligands, which facilitates the work-up. However, reaction times can be very long. Ullmann- and Buchwald–Hartwig-type methods have been used in intramolecular reactions, giving access to complex ring structures. All three N-arylation methods have specific advantages and disadvantages that should be considered when selecting the reaction conditions for a desired C–N bond formation in the course of a total synthesis or drug synthesis.

Direct Carbon−Carbon Bond Formation via Soft Enolization:  A Facile and Efficient Synthesis of 1,3-Diketones

2007 ◽  
Vol 9 (21) ◽  
pp. 4139-4142 ◽  
Author(s):  
Daniel Lim ◽  
Fang ◽  
Guoqiang Zhou ◽  
Don M. Coltart
Keyword(s):  
Bond Formation ◽  
Efficient Synthesis ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Soft Enolization
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