Desymmetric homologating annulation to access chiral pentafulvenes and their application in bioimaging

Sanjay Singh, Ravi Saini, Akshay Joshi, Neetu Singh and Ravi P. Singh ()
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Sanjay Singh: Indian Institute of Technology
Ravi Saini: Indian Institute of Technology
Akshay Joshi: Indian Institute of Technology Delhi
Neetu Singh: Indian Institute of Technology Delhi
Ravi P. Singh: Indian Institute of Technology

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract The architectural design of polycyclic/multisubstituted pentafulvenes has demonstrated great potential for the development of electrochromic materials and biologically active motifs. Unfortunately, the enantioselective construction of such distinctive cores with all carbon quaternary chiral centers has remained untouched to date. Herein, we disclose an enantioselective homologating annulation of cyclopent-4-ene-dione with 3-cyano-4-methylcoumarins through L-tert-leucine derived thiourea catalysis, affording a wide range of enantioenriched polycyclic multisubstituted embedded aminopentafulvenes with excellent stereocontrol (up to 99:1 er) and chemical yields up to 87%. A detailed photophysical and cytotoxicity analysis of racemic and chiral homologated adducts unveils the exceptional behavior of chiral adducts over their racemic analogs, highlighting the importance of stereoselectivity of the developed scaffolds. A cellular uptake experiment in a mammalian fibroblast cell line confirmed the potential of developed polycyclic aminopentafulvene cores as a highly promising labeling dye that can be utilized for bioimaging without any adverse effects.

Date: 2024
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DOI: 10.1038/s41467-024-45346-4

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