An easy and straightforward synthesis of 6,10b-diarylhexahydrobenzo[f]isoquinoline by the repeated treatment of boron trifluoride etherate (BF(3) x OEt(2)) is reported. The overall transformation from 4-arylpiperidin-3-one to benzo[f]isoquinoline proceeds via ring contraction, chain elongation, and intramolecular electrophilic cyclization in moderate yields.
Journal of the American Chemical Society, 131(2), 402-403 (2008-12-23)
C-H bond functionalization enables strategically new approaches to the synthesis of complex organic molecules including biologically active compounds, research probes and functional organic materials. To address the shortcomings of transition metal catalyzed processes, we have developed a new approach to
The Journal of organic chemistry, 74(6), 2605-2608 (2009-02-17)
A diastereoselective one-pot, three-component Prins-Friedel-Crafts reaction was developed for the synthesis of 4-aryltetrahydropyran derivatives from the reaction of carbonyl compounds with homoallylic alcohol in the presence of arene promoted by boron trifluoride etherate.
Twenty-one 4α-acyloxy-2-chloropodophyllotoxin derivatives (5a-u), whose C-4 spatial configuration was mainly stereocontrolled by the configuration of C-2 chlorine atom, were unexpectedly prepared by the reaction of 2-chloropodophyllotoxin with carboxylic acids in the presence of BF(3)·Et(2)O. Compared with ordinary esterifications of carboxylic
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