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Keywords:

  • allyl compounds;
  • azides;
  • Mitsunobu reaction;
  • nucleosides;
  • rearrangement
Thumbnail image of graphical abstract

Chilled out: Chiral allyl azides are rarely used in natural product synthesis because of their tendency to undergo a [3.3] sigmatropic rearrangement (see scheme, top). In allylic cyclopentenyl azides, this rearrangement can be suppressed at just 0 °C, enabling a short convergent synthesis of the hypermodified transfer-RNA nucleoside queuosine.