38568-50-2Relevant academic research and scientific papers
High Regio-, Chemo-, and stereoselectivity via low-temperature 4 + 3 cycloadditions. Convergent synthesis of multifunctionalized vinylmetals (M = Si, Sn) and S-vinyl benzenecarbothioates
Beck, Hartmut,Stark, Christian B. W.,Hoffmann, H. Martin R.
, p. 883 - 886 (2007/10/03)
(equation presented) A series of enantiomerically pure 8-oxabicyclo[3.2.1]oct-6-en-3-ones functionalized in the unsaturated two-carbon bridge has been prepared by the title reaction. Carbocation reactivity has been fined-tuned at -95 °C and adjusted to di
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.
