Stereoselective Synthesis of 2,4,5-Trisubstituted Piperidines via Radical Cyclization
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Colleges, School and Institutes
A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto alpha,beta-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2 to 40:1 when the radical stabilizing group is vinyl or phenyl. Cyclization of a (triethylsilyl)vinyl-stabilized radical gives the corresponding piperidine radical as a single diastereoisomer that may either be trapped by tributyltin hydride to afford the 2,4,5-trisubstituted piperidine or undergo a second 5-endo cyclization onto the (triethylsilyl)vinyl substituent to produce the 3,5,7-trisubstituted octahydropyrindene as a single diastereoisomer.
|Number of pages||11|
|Journal||The Journal of Organic Chemistry|
|Publication status||Published - 1 Nov 2010|