Sample presentation

1. [2,3] Wittig Rearrangement
Ross McKinney
Zach Wenker

2. Generalized [2,3] Sigmatropic
Rearrangement

3. Mechanism for [2,3] Wittig
Rearrangement

5. First Observation of a [2,3] Wittig
Rearrangement

6. Stereochemistry
• Strong preference for E isomer
• E alkene generally produces a threo
Z alkene generally produces an erythro
• Chirality is very specific
different conditions can create specific chiral
centers on different carbons

8. E isomer generally produces a threo
Z isomer generally produces an erythro

9. Use of [2,3] Wittig Rearrangement
• Because of its creation of a new pi bond and
sigma bond, as well as its stereospecifity, [2,3]
Wittig Rearrangements are widely used in the
synthesis of organic compounds.
• Examples include:
Synthesis of EF-Ring of Ciguatoxin 3C
Synthesis C18 Cecropia Juvenile Hormone

10. Synthesis of EF-Ring of Ciguatoxin 3C

11. Synthesis of C18 Cecropia Juvenile
Hormone

12. References
(1)Goto, A.; Fujiwara, K.; Kawai, A.; Kawai, H.;
Suzuki, T. Org. Lett. 2007, 9, 5373-5376.
(2)Nakai, Takeshi; Mikami, Koichi. Chem. Rev.
1986, 86(5), 885-902.
(3)Wittig, G.; Doser, H.; Justins Liebigs. Am.
Chem. 1949, 556, 192-205.
(4) Still. Tet. Lett. 1979, 593.