ol0c01142_si_001.pdf (6.05 MB)
Cubane Chirality via Substitution of a “Hidden” Regular Tetrahedron
Version 2 2020-05-22, 15:40
Version 1 2020-05-21, 20:44
journal contribution
posted on 2020-05-22, 15:40 authored by Nana Yoshino, Yumi Kato, Thibaud Mabit, Yuuya Nagata, Craig M. Williams, Mei Harada, Atsuya Muranaka, Masanobu Uchiyama, Seijiro MatsubaraIn the hexahedral
hydrocarbon cubane, replacing hydrogen with other
atoms at three positions within any one of the internal tetrahedrons
can conceptually lead to the formation of a unique class of chiral
molecules. In pursuit of this endeavor, we prepared 1,3-dibromo-4-deuteriocubane-N,N-diisopropylcarboxamide, which upon
treatment with zincates affords 1,3,5-trisubstituted cubanes via simultaneous
two-position substitution reactions. The proposed chiral attributes
of this stereogeometric class were confirmed by enantiomeric resolution
of a p-bromobenzyl derivative using chiral HPLC.