Pericyclic Reactions

The [2,3]-Wittig Rearrangement

[2,3]-Wittig Sigmatropic Rearrangements in Organic Synthesis
  Nakai, Chem. Rev. 1986, 86, 885-902.
Acyclic Stereocontrol via [2,3]-Wittig Sigmatropic Rearrangement,
   Mikami, K.; Nakai, T. Synthesis 1991, 594.
The [2,3]-Wittig Reaction,
   Nakai, T.; Mikami, K. Org. React. 1995, 46, 105-210.
Asymmetric [2,3]-Wittig Rearrangement as a General Tool for Asymmetric Synthesis,
   Nakai, T.; Tomooka, K. Pure Appl. Chem. 1997, 69, 595-600.
The Aza-Wittig Rearrangement,
   Vogel, C. Synthesis 1997, 497-505.


 

The reaction is a suprafacial process: Acutiphycin: Smith, A. B.; Chen, S. S.-Y.; Nelsom, F.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1997, 119, 10935. DOI

 

Punctatin A: Paquette, L. A.; Sugomura, T. J. Am. Chem. Soc. 1987, 109, 3017

 

  The [2,3]-Wittig rearrangement occurs with inversion of configuration at the metalated carbon: Hoffmann Angew. Chem. Int. Ed 1992, 31, 647; Cohen J. Am. Chem. Soc. 1992, 114, 375