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Efficient Synthesis of β‐Hydroxy Ketones from Allylic Alcohols by Catalytic Formation of Ruthenium Enolates
Author(s) -
Bartoszewicz Agnieszka,
Livendahl Madeleine,
MartínMatute Belén
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801690
Subject(s) - ruthenium , allylic rearrangement , isomerization , ketone , chemistry , aldol reaction , catalysis , protonation , domino , ligand (biochemistry) , combinatorial chemistry , organic chemistry , ion , biochemistry , receptor
The most efficient Ru‐catalyzed isomerization–aldol reaction from allylic alcohols has been achieved by using [η 5 ‐(Ph 5 Cp)Ru(CO) 2 Cl] as the catalyst. The bulky pentaphenylcyclopentadienyl ligand on the ruthenium atom prevents protonation at the oxygen of the Ru–enolate intermediate and completely suppresses the formation of unwanted ketone byproducts (see scheme). The domino transformation is as good as it can be: aldols are obtained in quantitative yields at ambient temperature.