Metal-catalyzed amide bond forming reactions in an environmentally friendly aqueous medium: nitrile hydrations and beyond

2013 ◽  
Vol 15 (1) ◽  
pp. 46-66 ◽  
Author(s):  
Rocío García-Álvarez ◽  
Pascale Crochet ◽  
Victorio Cadierno
Keyword(s):  
Aqueous Medium ◽  
Environmentally Friendly ◽  
Amide Bond ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
Metal Catalyzed

scholarly journals Minimizing HCN in DIC/Oxyma-Mediated Amide Bond-Forming Reactions

2020 ◽  
Vol 24 (7) ◽  
pp. 1341-1349 ◽  
Author(s):  
Marion Erny ◽  
Marika Lundqvist ◽  
Jon H. Rasmussen ◽  
Olivier Ludemann-Hombourger ◽  
Frédéric Bihel ◽  
...  
Keyword(s):  
Amide Bond ◽  
Bond Forming ◽  
Bond Forming Reactions

Are Aminomethyl Thioesters Viable Intermediates in Native Chemical Ligation Type Amide Bond Forming Reactions?

2018 ◽  
Vol 71 (9) ◽  
pp. 697
Author(s):  
Carlie L. Charron ◽  
Jade M. Cottam Jones ◽  
Craig A. Hutton
Keyword(s):  
Amide Bond ◽  
Native Chemical Ligation ◽  
Direct Reaction ◽  
Chemical Ligation ◽  
Bond Forming ◽  
Type Process ◽  
Bond Forming Reactions ◽  
Subsequent Conversion ◽  
Three Component Coupling

The condensation of N-mercaptomethyl amines and thioesters is a potential route to amides, via aminomethyl thioester intermediates, in a native chemical ligation type process followed by self-cleavage of the ‘mercaptomethyl’ auxiliary. This paper describes investigations towards the preparation of aminomethyl thioesters, and subsequent conversion into amides, from a three-component coupling of formaldehyde, a thioacid, and an amine. Our studies suggest that while such intermediates may be formed en route to amides, no advantages are offered over the direct reaction of the amine and thioacid precursors.

Metal-mediated C–O bond forming reactions in natural product synthesis

2017 ◽  
Vol 4 (12) ◽  
pp. 2480-2499 ◽  
Author(s):  
Gwilherm Evano ◽  
Jianjun Wang ◽  
Antoine Nitelet
Keyword(s):  
Natural Product ◽  
Critical Review ◽  
Natural Product Synthesis ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Metal catalyzed reactions for the formation of C(sp2)–O bonds have had a dramatic impact in natural product synthesis. They have enabled the emergence of new bond disconnections, which notably resulted in remarkably efficient and short synthetic pathways. The use of these reactions for the formation of C–O bonds in natural product synthesis is overviewed in this critical review.

The Stereochemistry of Organometallic Compounds. XXIX. Synthesis of Steroidal 1,4-Diphosphine, 1,3-Diphosphine and 1,6-Diphosphine and Their Evaluation as Ligands in Metal Catalyzed Asymmetric Synthesis

1987 ◽  
Vol 40 (6) ◽  
pp. 1083 ◽  
Author(s):  
RJ Thomson ◽  
WR Jackson ◽  
D Haarburger ◽  
EI Klabunovsky ◽  
VA Pavlov
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Hydrogenation ◽  
Organometallic Compounds ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Hydrogenation Reactions ◽  
Metal Catalyzed ◽  
Asymmetric Carbon

The steroidal 1,4-diphosphines 3α- and 3β-diphenylphosphino-2a-(2'-diphenylphosphinoethyl)-5α-cholestanes and their 5H-benzo[b] phosphindole derivatives have been prepared and shown to be useful ligands in asymmetric hydrogenation reactions. Interestingly the 3α- and 3β-derivatives lead to opposing enantioselection preferences when used in these reactions. A steroidal 1,3-diphosphine, 3α-diphenylphosphino-2α-diphenylphosphinomethyl-5α-cholestane, has been prepared as a mixture containing some of the 3β-epimer. The 3α-1,3-diphosphine led to similar enantioselection in hydrogenation reactions as the 3α-1,4-diphosphine, and a model is proposed to explain the sense of the enantioselectivity in the 1,4- and 1,3-diphosphines. A steroidal 1,6-diphosphine has also been prepared but leads to lower optical yields in the hydrogenation reactions. These ligands have been shown to lead to only poor to moderate optical yields when used in asymmetric carbon-carbon bond forming reactions.

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