2-Cyclohexene-1-carboxylic acid, 4-oxo-, methyl ester

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CAS: 67201-30-3
MF: C8H10O3
MW: 154.1632
Synonyms: 2-Cyclohexene-1-carboxylic acid, 4-oxo-, methyl ester

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Finian Leeper

Cambridge University
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Co-reporter: James M. Kelly, Finian J. Leeper
pp: 819-821
Publication Date(Web):15 February 2012
DOI: 10.1016/j.tetlet.2011.12.013
The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic α,β-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles.Image for unlabelled figure