Abstract
A wide variety of stabilized carbanions have been found to participate as nucleophiles in intramolecular Michael-type conjugate additions to in situ generated nitrosoalkenes to form bridged carbocyclic systems. The vinylnitroso platforms for these cyclizations have been prepared via two key steps involving ring-closing metathesis of vinyl chlorides and regioselective conversion of vinyl chlorides to α-chloroketones with sodium hypochlorite in glacial acetic acid/acetone. An alternative approach to preparation of some cyclization substrates has involved use of more reactive enol ethers as precursors to the requisite α-chloroketones. A sulfonamide anion has also been found to be an effective nucleophile in this type of reaction, leading to formation of a 6-azabicyclo[3.2.1]octane.
Original language | English (US) |
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Pages (from-to) | 2094-2101 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 76 |
Issue number | 7 |
DOIs | |
State | Published - Apr 1 2011 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry