Homologation of Monoterpenoids into New Sesquiterpenoids  via  Tandem Isomerisation/Claisen Rearrangement Reactions with Three‐Component Ruthenium Catalysts, and Ru(methallyl) 2 (COD) Revealed by High Throughput Screening Techniques | Zendy

Le Nôtre Jérôme | Zendy; Touzani Rachid | Zendy; Lavastre Olivier | Zendy; Bruneau Christian | Zendy; Dixneuf Pierre H. | Zendy

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Homologation of Monoterpenoids into New Sesquiterpenoids via Tandem Isomerisation/Claisen Rearrangement Reactions with Three‐Component Ruthenium Catalysts, and Ru(methallyl) 2 (COD) Revealed by High Throughput Screening Techniques

Author(s) -

Le Nôtre Jérôme,

Touzani Rachid,

Lavastre Olivier,

Bruneau Christian,

Dixneuf Pierre H.

Publication year - 2005

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.200404391

Subject(s) - chemistry , ruthenium , isomerization , catalysis , tandem , claisen rearrangement , ligand (biochemistry) , reagent , aldehyde , organic chemistry , combinatorial chemistry , medicinal chemistry , biochemistry , materials science , receptor , composite material

A catalytic system B based on a ruthenium source Ru 3 (CO) 12 , a bulky imidazolinium salt and Cs 2 CO 3 appears very efficient for the transformation of a 1,7‐diene into a γ,δ‐unsaturated aldehyde via tandem isomerisation/Claisen reactions. 1,6‐Dienes arising from the terpenoids menthone and myrtenal were selectively transformed into the corresponding unsaturated aldehydes with catalyst B . High throughput experiments were undertaken to evaluate other multicomponent catalysts: metal source/ligand/base for these tandem reactions. An unexpected catalyst was found to be Ru(methallyl) 2 (COD) which can operate without additional ligand or reagent.

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