209852-85-7Relevant academic research and scientific papers
Chiral Allyl Cations Are Capture by Furan with 100% Stereoselectivity: Synthesis of Enantiopure 2-Alkoxy-8-oxabicyclo[3.2.1]oct-6-en-3-ones by Low-Temperature [4+3] Cycloaddition
Stark, Christian B. W.,Pierau, Sabine,Wartchow, Rudolf,Hoffmann
, p. 684 - 691 (2007/10/03)
A low-temperature (-95°C) protocol for intermolecular cycloadditions of furan to chiral silyloxyallyl cations in dichloromethane is described. Key precursors are open-chain, mixed α-ketoacetals, which are chiral. The resulting [4+3] cycloadducts are dense
Chiral allyl cations in cycloadditions to furan: Synthesis of 2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one in high enantiomeric purity
Stark, Christian B. W.,Eggert, Ulrike,Hoffmann
, p. 1266 - 1268 (2007/10/03)
Efficient shielding of the π face is offered by the phenyl group of the chiral auxiliary (TES = triethylsilyl) to the allyl cation generated at low temperature from 1. This protection induces high π-facial selectivity and allows high chemical yield on the capture of the cation by furan to afford the title cycloadduct 2.
