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Diastereoselective Synthesis of Diquinanes and Triquinanes Bearing Vicinal Quaternary Carbon Stereocenters from Acyclic Allene-based Precursors via a Cascade Reaction

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journal contribution
posted on 11.08.2017, 18:33 by Shuang Li, Pengpeng Zhang, Yuanhe Li, Shumin Lu, Jianxian Gong, Zhen Yang
A cascade benzenethiol-mediated intramolecular [3 + 2] cycloaddition reaction between an allene and an α,β-unsaturated aldehyde or ester is developed for the diastereoselective synthesis of [3.3.0] bicyclic system bearing two quaternary atoms at their bridgehead positions. Notably, these structurally complex systems can be found in a wide range of natural products.