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Ruthenium Catalyzed Selective Regio‐and‐Mono‐Allylation of Cyclic 1,3‐Diketones Using Allyl Alcohols as Substrates
Author(s) -
Gruber Stefan,
Pregosin Paul S.
Publication year - 2009
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.200900568
Subject(s) - chemistry , ruthenium , allyl alcohol , allylic rearrangement , catalysis , sulfonate , yield (engineering) , alcohol , substrate (aquarium) , medicinal chemistry , organic chemistry , regioselectivity , dimedone , sodium , materials science , oceanography , metallurgy , geology
The new ruthenium‐sulfonate catalyst Ru(Cp*)(η 3 ‐C 3 H 5 ) ( p ‐CH 3 C 6 H 4 SO 3 ) 2 , (Cp*=pentamethylcyclopentadienyl), rapidly and regioselectively mono‐allylates dimedone to the branched products using substituted allyl alcohols as substrates, without acid, base or other additives, under relatively mild conditions. We consider the ruthenium sulfonate to be a “green” alternative in that it uses allyl alcohols as substrate, (rather than carbonates, acetates, etc.) and therefore does not waste the leaving group. The catalyst induces rapid double allylation of various 1,3‐diketones in high yield using allylic alcohol.