Stereoselection in the Prins-Pinacol Synthesis of Acyltetrahydrofurans
Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.
Additional Information© 2001 American Chemical Society. Received 12 February 2001. Published online 23 March 2001. Published in print 1 April 2001. This research was supported by a Javits Neuroscience Investigator Award from NIH NINDS (NS-12389). Merck, Pfizer, Roche Biosciences, and SmithKline Beecham provided additional support. NMR and mass spectra were determined using instruments acquired with the assistance of NSF and NIH shared instrumentation grants.
Supplemental Material - ol0157003_s1.pdf