Abstract
New bicyclo[3.2.1]octanes are easily prepared in a few steps from norbornene. The key reaction in this process is the tandem isomerization- intramolecular aldol reaction from lactol 4 and/ or allylic alcohol 5, mediated by transition-metal catalysts. This reaction affords bicyclic derivative 6 as a single stereoisomer and the stereoselectivity of this process could be explained by analysis of the different transition states using high-level computational studies. The key intermediate enone 7 is easily obtained from 6 through the corresponding mesylate. The synthetic potential of bicyclic enone 7 is illustrated with several examples. © Georg Thieme Verlag Stuttgart.
Original language | English |
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Pages (from-to) | 1969-1973 |
Journal | Synlett |
Issue number | 12 |
DOIs | |
Publication status | Published - 1 Jul 2009 |
Keywords
- Aldol
- Allylic alcohols
- Bicycloalkenones
- Catalyst
- DFT calculations