Cubane Chirality via Substitution of a "Hidden" Regular Tetrahedron

In 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-diisopropyl...

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Published inOrganic letters Vol. 22; no. 11; pp. 4083 - 4087
Main Authors Yoshino, Nana, Kato, Yumi, Mabit, Thibaud, Nagata, Yuuya, Williams, Craig M., Harada, Mei, Muranaka, Atsuya, Uchiyama, Masanobu, Matsubara, Seijiro
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.06.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MEDICINAL CHEMISTRY
METALATION
BOND
DISCOVERY
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Summary:In 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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01142