Enantiomerically pure poly(oxymethylene) helices: correlating helicity with centrochirality
- Autor(en)
- Simon Eppacher, Gerald Giester, Jan W. Bats, Christian Noe
- Abstrakt
A first series of enantiomerically pure helical oligo(formaldehyde)s (¼oligo(oxymethylen)s) 16 – 20was synthesized. To induce the chiral uniformity of the helices, we used (1S)-2,2-dimethyl-1-phenylpropan-1-ol (14) to generate the end groups at the a and w terminus (Scheme 6). Propanol 14 wasaccessible from its racemate by acetal formation with lactol 12 and separation of the diastereoisomers(Scheme 5). The helicity of the oligomers was investigated by temperature-dependent CD, NMR, andoptical-rotation studies. In addition to qualitative considerations concerning the helicity of oligo(formaldehyde)s, we performed calculations of the dimer 17 and the pentamer 20 as well as X-ray structureanalyses of the dimer 17 and the tetramer 19 to establish the handedness of the helices and to correlatetheir sense with the absolute configuration of the inducing stereogenic center. The results may be ofrelevance with respect to induction and propagation of chirality in prebiotic chemistry.
- Organisation(en)
- Institut für Mineralogie und Kristallographie
- Externe Organisation(en)
- Johann Wolfgang Goethe-Universität Frankfurt am Main
- Journal
- Helvetica Chimica Acta
- Band
- 91
- Seiten
- 581-597
- Anzahl der Seiten
- 17
- ISSN
- 0018-019X
- Publikationsdatum
- 2008
- Peer-reviewed
- Ja
- ÖFOS 2012
- 105113 Kristallographie, 3012 Pharmazie, Pharmakologie, Toxikologie
- Link zum Portal
- https://ucrisportal.univie.ac.at/de/publications/3f31d039-56c8-40b6-9950-bfca2ed1c805