Format

Send to:

Choose Destination
See comment in PubMed Commons below
Chemistry. 2013 Dec 2;19(49):16722-8. doi: 10.1002/chem.201302479. Epub 2013 Oct 31.

Diastereo- and enantioselective synthesis of organometallic bis(helicene)s by a combination of C-H activation and dynamic isomerization.

Author information

  • 1Sciences Chimiques de Rennes, UMR 6226, Institut de Physique de Rennes, UMR 6251, CNRS Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex (France).

Abstract

Homochiral and heterochiral cis-bis-cycloplatinated-[6]helicene derivatives 1b(1,2), as representative examples of platina[6]helicenes that share a common platinum center, have been prepared. A diastereo- and enantioselective synthesis, which combines CH activation and dynamic isomerization from heterochiral structure 1b(2) into homochiral structure 1b(1), is also described. Overall, this isomerization process results in the transfer of chiral information from one helicene moiety to the other one. The chiroptical properties of homochiral (P)- and (M)-1b(1) were greatly modified upon oxidation into their corresponding (P)- and (M)-diiodo-Pt(IV) complexes (5). The changes were also analyzed by performing theoretical calculations. C-H activation in the synthesis of organometallic helicenes is further demonstrated by the preparation of cis-bis-cycloplatinated-[8]helicene 1c.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

CH activation; chiroptical properties; density functional calculations; helicenes; isomerization

PMID:
24173674
[PubMed]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for John Wiley & Sons, Inc.
    Loading ...
    Write to the Help Desk