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Diastereo- and regioselective petasis aryl and allyl boration of ninhydrins towards synthesis of functionalized indene-diones and dihydrobenzoindeno-oxazin-ones

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Abstract

Petasis aryl and allyl borations were accomplished using substituted ninhydrins, boronic acids or 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 1,2-aminophenols in Hexafluoroisopropanol (HFIP) without any catalysts to synthesize different aryl and allyl derivatives of ninhydrins. The nature of substitution in the boronic acids and 1,2-amino phenols was the key factor in determining the diastereo-regioselectivity and the type of product distributions. The products were isolated and characterized by HMBC, HSQC, 1H, 13C NMR experiments and X-ray single crystallographic analysis. A probable reaction pathway involves in situ formation of acyclic and cyclic ninhydrin-amino alcohol adducts, with the positioned hydroxyl group determining the stereo-regioselective outcome via tetracoordinated boron intermediates.

Graphical abstract

A metal free diastereo- and regioselective Petasis aryl and allyl boration of ninhydrins.

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Acknowledgements

We gratefully acknowledge The University of Calcutta and TCG Lifesciences Pvt. Ltd., India for this collaborative research. We also like to thank CAS-V (UGC), DST-FIST, and DST-PURSE, Department of Chemistry, University of Calcutta for funding as departmental projects.

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Authors and Affiliations

  1. Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata, 700009, India

    Ayon Sengupta & Chhanda Mukhopadhyay

  2. TCG Lifesciences Pvt. Ltd., BN 7, Sector V, Salt Lake City, Kolkata, 700091, India

    Ayon Sengupta & Sonali Rudra

  3. Department of Chemistry, R.K. Mission Residencial College, Narendrapur, Kolkata, 700103, India

    Suvendu Maity, Pinaki Saha & Prasanta Ghosh

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  1. Ayon Sengupta
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Sengupta, A., Maity, S., Saha, P. et al. Diastereo- and regioselective petasis aryl and allyl boration of ninhydrins towards synthesis of functionalized indene-diones and dihydrobenzoindeno-oxazin-ones. Mol Divers 27, 1385–1400 (2023). https://doi.org/10.1007/s11030-022-10496-4

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