Four-Component Assembly of Chiral N-B Heterocycles with a Natural Product-Like Framework

Francesco Montalbano, Nuno R. Candeias, Luis F. Veiros, Vania Andre, M. Teresa Duarte, Maria R. Bronze, Rui Moreira, Pedro M. P. Gois

    Research output: Contribution to journalArticleScientificpeer-review

    23 Citations (Scopus)

    Abstract

    The dative N-B bond was used to simply assemble heterocycles with a skeleton akin to the 5-oxofuro[2,3-b]furan motif. Twenty-five new N-B heterocycles were prepared via a highly efficient one-pot four-component reaction in yields and diastereoselectivities up to 95% and >97%, respectively. Several reaction intermediates were discovered using electrospray ionization mass spectroscopy which set the basis for the mechanism elucidation using DFT calculations.

    Original languageEnglish
    Pages (from-to)988-991
    Number of pages4
    JournalOrganic Letters
    Volume14
    Issue number4
    DOIs
    Publication statusPublished - 17 Feb 2012
    Publication typeA1 Journal article-refereed

    Funding

    Fundacao para a Ciencia e Tecnologia (PTDC/QUI-QUI/118315/2010; PTDC/QUI-QUI/099389/2008; FRH/BPD/46589/2008;/48219/2008; Pest-OE/SAU/UI4013/2011; PEst-OE/QUI/UI0100/2011) are acknowledged for financial support.

    Keywords

    • BORON
    • COMPLEXES
    • NITROGEN

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