Open AccessGrubbs Cross-Metathesis Pathway for a Scalable Synthesis of γ-Keto-α,β-unsaturated Esters
Author(s) -
Reji Nair,
Thomas D. Bannister
Publication year - 2014
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo4023606
Subject(s) - chemistry , metathesis , allylic rearrangement , salt metathesis reaction , olefin metathesis , yield (engineering) , organic chemistry , grubbs' catalyst , catalysis , combinatorial chemistry , polymerization , polymer , materials science , metallurgy
A direct and scalable route to γ-keto-α,β-unsaturated esters, useful intermediates in medicinal chemistry and natural products synthesis, is reported. The key step involves the use of Grubbs' second-generation olefin metathesis catalyst for cross-metathesis of alkyl acrylates and 2° allylic alcohols. The metathesis step is followed by oxidation to give the desired products in high yield on scales of up to 25 g.
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