Synthesis of thiahydrindanones and thiadecalones by Dieckmann cyclization: The stereochemistry of thiolate anion addition to cyclohexenes

The synthesis of trans-3-thiadecal-1-one (5) and cis-3-thiahydrindan-1-one (12) by Dieckmann cyclization (DC) is described. Anions of mercapto-esters are shown to add to activated cyclohexenes in a trans diaxial fashion in kinetically controlled Michael additions (MA). An explanation is presented for the retro-MA of cis-1-(2i-ethoxycarbonylethylthio)-2-ethoxycarbonylcyclohexane (10) under DC-conditions.

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