Combined directed ortho metalation-cross coupling strategies. Design for natural product synthesis

1994 ◽  
Vol 66 (10-11) ◽  
pp. 2155-2158 ◽  
Author(s):  
V. Snieckus
Keyword(s):  
Natural Product ◽  
Cross Coupling ◽  
Natural Product Synthesis ◽  
Ortho Metalation ◽  
Coupling Strategies

ChemInform Abstract: Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis

ChemInform ◽  
2016 ◽  
Vol 47 (50) ◽  
Author(s):  
Natasha F. O'Rourke ◽  
Matthew J. Kier ◽  
Glenn C. Micalizio
Keyword(s):  
Natural Product ◽  
Cross Coupling ◽  
Natural Product Synthesis

scholarly journals Metallacycle-mediated cross-coupling in natural product synthesis

Tetrahedron ◽  
2016 ◽  
Vol 72 (45) ◽  
pp. 7093-7123 ◽  
Author(s):  
Natasha F. O'Rourke ◽  
Matthew J. Kier ◽  
Glenn C. Micalizio
Keyword(s):  
Natural Product ◽  
Cross Coupling ◽  
Natural Product Synthesis

scholarly journals σ-Bond Hydroboration of Cyclopropanes

2020 ◽  
Author(s):  
Hiroki Kondo ◽  
Shin Miyamura ◽  
Chisa Kobayashi ◽  
Arifin ◽  
Stephan Irle ◽  
...  
Keyword(s):  
Double Bond ◽  
Natural Product ◽  
Organic Synthesis ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
High Reactivity ◽  
Natural Product Synthesis ◽  
Theoretical Studies ◽  
Single Bond

Hydroboration of alkenes is a classical reaction in organic synthesis, in which alkenes react with boranes to give alkylboranes, with subsequent oxidation resulting in alcohols. The double bond (π-bond) of alkenes can be readily reacted with boranes owing to its high reactivity. However, the single bond (σ-bond) of alkanes has never been reacted. To pursue the development of σ-bond cleavage, we selected cyclopropanes as model substrates since they present a relatively weak σ-bond. Herein, we describe an iridium-catalyzed hydroboration of cyclopropanes, resulting in β-methyl alkylboronates. These unusually branched boronates can be derivatized by oxidation or cross-coupling chemistry, accessing “designer” products that are desired by practitioners of natural product synthesis and medicinal chemistry. Furthermore, mechanistic investigations and theoretical studies revealed the enabling role of the catalyst.

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