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

• DOI: 10.1021/acs.orglett.7b01733
• Publication Date: 2017-08-11T18:39:54Z
• Authors: Shuang Li; Pengpeng Zhang; Yuanhe Li; Shumin Lu; Jianxian Gong; Zhen Yang
• Keywords: Stereocenter; Allene; Cascade reaction; Vicinal; Quaternary carbon

A cascade benzenethiol-mediated intramolecular [3 + 2] cycloaddition reaction between an allene and 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 natural products.