Premium
Regioselective Cobalt‐Catalysed Hydrovinylation for the Synthesis of Non‐Conjugated Enones and 1,4‐Diketones
Author(s) -
Kersten Laura,
Hilt Gerhard
Publication year - 2012
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.201100800
Subject(s) - chemistry , regioselectivity , enol , aldol reaction , enol ether , ozonolysis , stereospecificity , silyl ether , silylation , silyl enol ether , organic chemistry , conjugated system , hydrolysis , cobalt , catalysis , polymer
The highly regioselective cobalt‐catalysed 1,4‐hydrovinylation of terminal alkenes with 2‐trimethylsilyloxy‐1,3‐butadiene generates in a stereospecific fashion unsaturated E‐ configured silyl enol ether intermediates that are suitable for diastereoselective Mukaiyama‐aldol reactions with bulky aliphatic aldehydes. The acidic hydrolysis of the enol ethers to γ,δ‐unsaturated ketones followed by ozonolysis can be used for the synthesis of various 1,4‐diketones and polycarbonyl derivatives. The 1,4‐diketones and polycarbonyl derivatives were successfully tested for the synthesis of some mono‐ and bis‐pyrrole derivatives. The γ,δ‐unsaturated ketones are useful building blocks (e.g., in natural product synthesis) and can be generated in a one‐pot procedure.