Abstract
A novel approach to 3-substituted 4-piperidinones is described. The one-pot tandem oxidation - cyclization - oxidation of unsaturated alcohols 1a-e by PCC or PCC and trifluoromethanesulfonic acid affords piperidinones 2a-e in good yield. Reduction of 2a-e by L-Selectride gives the corresponding cis 3,4-disubstituted piperidines with diastereomeric ratios of >99:1. By contrast, reduction of 2a-e by Al-isopropoxydiisobutylalane gives the trans products with diastereomeric ratios of up to 99:1.
Original language | English |
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Pages (from-to) | 3226-3229 |
Number of pages | 4 |
Journal | The Journal of Organic Chemistry |
Volume | 69 |
Issue number | 9 |
DOIs | |
Publication status | Published - 30 Apr 2004 |