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.

1,2-Dihaloalkenes in Metal-Catalyzed Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (16) ◽  
pp. 3087-3113 ◽  
Author(s):  
Benoit Daoust ◽  
Nicolas Gilbert ◽  
Paméla Casault ◽  
François Ladouceur ◽  
Simon Ricard
Keyword(s):  
Transition Metal ◽  
Building Blocks ◽  
Facile Synthesis ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

1,2-Dihaloalkenes readily undergo simultaneous or sequential difunctionalization through transition-metal-catalyzed reactions, which makes them attractive building blocks for complex unsaturated motifs. This review summarizes recent applications of such transformations in C–C and C–heteroatom bond forming processes. The facile synthesis of stereodefined alkene derivatives, as well as aromatic and heteroatomic­ compounds, from 1,2-dihaloalkenes is thus outlined.1 Introduction2 Synthesis of 1,2-Dihaloalkenes3 C–C Bond Forming Reactions4 C–Heteroatom Bond Forming Reactions5 Conclusion

Formation of tetrasubstituted C–C double bonds via olefin metathesis: challenges, catalysts, and applications in natural product synthesis

2018 ◽  
Vol 5 (3) ◽  
pp. 494-516 ◽  
Author(s):  
Nirmalya Mukherjee ◽  
Sebastian Planer ◽  
Karol Grela
Keyword(s):  
Transition Metal ◽  
Natural Product ◽  
Olefin Metathesis ◽  
Natural Product Synthesis ◽  
Synthetic Chemistry ◽  
Double Bonds ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
The Many

Among the many types of transition-metal-catalysed C–C bond forming reactions, olefin metathesis is without a doubt one of the most thriving fields in modern organic synthetic chemistry.

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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