Chiral Buckybowl

This enantioselective synthesis of chiral trimethylsumanene demonstrated the wide applicability of the solution-phase method, especially the strategy to utilize the less strained nonconjugated bowl structure for the construction of the more strained conjugated bowl structure. The versatility of this approach was also well demonstrated in the enantioselective synthesis of chiral triazasumanene discussed 

---

The enantioselective synthesis of a chiral buckybowl was reported by Sakurai and Higashibayashi in 2008 [145]. As in the synthesis of sumanene, C3 symmetric iyn-tris(norbomeno)-benzene 126 is the key intermediate in this synthetic approach (Scheme 42). The synthesis started with enantiopure iodonorbomanone. The... 

The correlations between structures and bowl-to-bowl inversion barriers provide information on the inversion dynamics and design of a static bowl. Increase in the curve of buckybowls may also increase their molecular dipole moment. A high inversion barrier conveys a configurational stability to a chiral buckybowl, avoiding loss of enantiopurity through the bowl-inversion racemization process. 

The preparation, stabilization, and characterization of buckybowl anions, ranging from archetypal corannulene to large hemifullerenes, have been reviewed. The synthetic potential and configurational stability of configurationally labile chiral carbanions next to electron-withdrawing groups has been summarized. ... 

---