Abstract
The stereoselective construction of highly functionalized fiveand six-membered rings is an important synthetic goal since such ring skeletons are present in numerous natural products of biological interest.1,2 Recently, we have shown that intramolecular cyclization of (η-diene)Fe(CO)3 complexes bearing functionalized side chains at the terminal position of the diene ligands furnished bicyclo[3.3.0]octane and -[4.3.0]nonane ring units in the presence of carbon monoxide.3 We have now demonstrated that this methodology can be applied toward highly diastereoselective synthesis of trisubstituted cyclopentaneand cyclohexanecarboxylic acid derivatives by treatment of carboester functionalized (η4-diene)Fe(CO)3 complexes with lithium diisopropylamide (LDA) followed by in situ oxidation with molecular oxygen.
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