Abstract
A diastereodivergent synthesis of enantiopure cis- and trans-2-[(3-ethyl-4-piperidyl)methyl]indole ( cis- 1b and trans- 1b) from a common phenylglycinol-derived oxazolopiperidone lactam 3 is reported. The key step is a stereocontrolled conjugate addition, either under kinetic or thermodynamic control, of the dilithium salt of 2-(2-indolyl)-1,3-dithiane to unsaturated lactam 3.
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