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

作者：Li, Shuang; Zhang, Pengpeng; Li, Yuanhe; Lu, Shumin; Gong, Jianxian^*; Yang, Zhen^*

来源：Organic Letters, 2017, 19(17): 4416-4419.

DOI：10.1021/acs.orglett.7b01733

• CATALYZED 3+2 CYCLOADDITION
• ELECTRON-DEFICIENT OLEFINS
• RADICAL-CHAIN ADDITION
• FUNCTIONALIZED CYCLOPENTANES
• NATURAL-PRODUCTS
• PHOSPHINE
• CYCLIZATIONS
• ALLENYLSILANES
• ANNULATIONS
• ACCESS

A cascade benzenethiol-mediated intramolecular [3 + 2] cycloaddition reaction between an allene and an alpha,beta-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.

• 出版日期2017-9-1
• 单位北京大学; 北京大学深圳研究生院