Cubane Chirality via Substitution of a 'Hidden' Regular Tetrahedron
| Autor: | Yumi Kato, Mei Harada, Seijiro Matsubara, Masanobu Uchiyama, Nana Yoshino, Atsuya Muranaka, Thibaud Mabit, Yuuya Nagata, Craig M. Williams |
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| Rok vydání: | 2020 |
| Předmět: |
Substitution reaction
010405 organic chemistry Chemistry Organic Chemistry Substitution (logic) 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Chiral column chromatography chemistry.chemical_compound Crystallography Cubane Tetrahedron Physical and Theoretical Chemistry Enantiomer Chirality (chemistry) Derivative (chemistry) |
| Zdroj: | Organic Letters. 22:4083-4087 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.0c01142 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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