Abstract
Treatment of the azabicyclo[2.2.1]heptene derivative 4 with mCPBA for 3-5 seconds generates the oxazabicyclo[3.2.1]octene derivative 7 (X-ray structure) via rapid Meisenheimer rearrangement of the N-oxide 5, whilst heating 7 in MeCN for 4-6 h leads to further rearrangement to the more thermodynamically stable oxazabicyclo[3.3.0]octene isomer 6; 6 and 7 can be readily reduced to enantio-pure hydroxylated cyclopentylglycine derivatives.
Original language | English |
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Pages (from-to) | 2451-2452 |
Number of pages | 2 |
Journal | Chemical Communications |
Issue number | 24 |
DOIs | |
Publication status | Published - 21 Dec 2000 |