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Chiral Allyl Cations in Cycloadditions to Furan: Synthesis of 2-(1'-Phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one
Christian B W Stark1, Ulrike Eggert1, H M R Hoffmann1
1Department of Organic Chemistry, University of Hannover, Schneiderberg 1 B, D-30167 Hannover (Germany), Fax: Int. (+49) 511-762-3011.
Angewandte Chemie (International Ed. in English)
|May 2, 2018
Abstract:
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.