Dynamic Chirality Control of tropos DPCB-digold Skeleton by Chiral Binaphthyldicarboxylate

Chemistry, an Asian Journal
Shigekazu ItoKoichi Mikami

Abstract

The planar 3,4-diphosphinidenecyclobutene (DPCB) can be remarkably twisted into a C2 -type helical structure by dual coordination of a AuCl moiety. A prompt chirality control of the twisted DPCB skeleton ligated by the digold units affords the enantiopure structure by exchanging the chloride ligands for chiral [1,1'-binaphthalene]-2,2'-dicarboxylate. The chirality of the diaurated 2,2'-bis(diphenylphosphanyl)-1,1'-biphenyl (BIPHEP) system can be controlled prior to that of DPCB. Mixing of a DPCB-bis(chlorogold) complex with the chiral silver salt dynamically leads to a single diastereomer, which was characterized by the (31) P NMR spectrum and the CD couplet patterns in the visible (DPCB) area. The absolute configuration of the singly induced helical structure was assigned by the theoretical CD spectra determined by TD-DFT calculations. Intramolecular alkoxycyclization of hexa-4,5-dien-1-ol catalyzed by the asymmetric DPCB-digold structure were also attempted.

References

Jun 6, 2000·Advanced Drug Delivery Reviews·H R Hoogenboom de Haard H
Nov 25, 2000·Angewandte Chemie·K MikamiR Angelaud
Aug 14, 2003·Chemical Reviews·Koichi Mikami, Masahiro Yamanaka
Oct 25, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Fumiyuki Ozawa, Masaaki Yoshifuji
May 14, 2009·Angewandte Chemie·Pilar García-GarcíaBenjamin List
Nov 10, 2009·Chemistry : a European Journal·A Stephen K HashmiJan W Bats
Oct 6, 2012·Chemical Communications : Chem Comm·Kohsuke Aikawa, Koichi Mikami
Nov 16, 2013·Accounts of Chemical Research·Yi-Ming WangF Dean Toste
Oct 6, 2015·Chemical Communications : Chem Comm·Marta Ayerbe GarciaRené Peters

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Citations

Jan 17, 2020·ChemPlusChem·Tomokazu ShinozakiShigekazu Ito
Oct 21, 2020·Chemistry : a European Journal·Miki KatoShigekazu Ito

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