Citation that was cited by Peng et. al.:
Still, C.; Mitra, A. J. Am. Chem. Soc. 1978, 100, 1927-1928.
Still and Mitra discovered that the [2,3]-Wittig rearrangement has a transition state that prefers pseudoaxial substitution, showing that [2,3] and [3,3] sigmatropic rearrangements do not have general pseudoequatorial substitution. The authors reported this discovery through a [2,3]-Wittig rearrangement that produces Z-trisubstituted homoallylic alcohols in high yields and with ≥95% stereoselectivity. The alkylation of allylic alcohol with iodomethyltributyltin shows that transition state A, having a pseudoaxial butyl substituent, is strongly preferred over transition state B due to the less severe butyl/vinyl methyl interaction in B. Still and Mitra concluded that [2,3]-Wittig rearrangements has high stereoselectivity for Z-trisubstituted olefins and most trisubstituted olefin synthesis produce E isomers as major products.
Alkylation of allylic alcohol with iodomethyltributyltin
Transition states A and B
Additional references that cited the reference above:
Millar, J. G.; Moreira, J. A.; McElfresh, J. S.; Daane, K. M.; Freund, A. S. Org. Lett. 2009, 11, 2683-2685.
This paper used the [2,3]-sigmatropic rearrangement to obtain a sterically congested
tetraalkylcylopentene framework for constructing the sex pheromone of the longtailed mealybug.
Blackburn, T. J.; Helliwell, M.; Kilner, M. J.; Lee, A. T. L.; Thomas, E. J. Tetrahedron Lett. 2009, 50, 3550-3554.
The authors of this paper used the stereoselective [2,3]-Wittig rearrangement to prepare the carbon skeleton of phomactins, which “possess interesting biological activity including platelet activating factor antagonism.”
Tanaka, K.; Nakamura, Y.; Sasaki, A.; Ueda, R.; Suzuki, Y.; Kuwahara, S.; Kiyota, H. Tetrahedron 2009, 65, 6115-6122.
The authors of this paper used [2,3]-Wittig rearrangement as the beginning step of this synthesis in order to construct a carbon framework for the rest of the synthesis of enantiomers and racemate of pyricuol, a phytotoxin isolated from the rice blast disease fungus, Magnaporthe grisea.