Borane and alane reductions of bulky N,N′-diaryl-1,3-diimines: Structural characterization of products and intermediates in the diastereoselective synthesis of 1,3-diamines

David T. Carey, Francis S. Mair, Robin G. Pritchard, John E. Warren, Rebecca J. Woods

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Two new C2-symmetric diazaborinanes were prepared by diastereoselective intramolecular dihydroboration of bulky 1,3-diamines, the remarkably stable l-[HB(2,6-Pr2i-C6H3 NCHMe)2CMe2], from which it was not possible to isolate free diimine, and the less bulky l-[HB(2-Pri-C6 H4NCHMe)2CMe2], which yielded l-(2-Pri-C6H4NHCHMe)2 CMe2 on acid work up. The BH3 reductions were highly diastereoselective for l-products (de > 95%). Use of AlCl3/LiAlH4 mixtures in diethyl ether gave lower (de ≈ 75%) and opposite selectivity, yielding predominantly u-(2,6-Pr2i - C6H3NHCHMe)2CMe2 upon work up, via a u-[H2Al(2,6-Pr2i- C6H3)NHCHMeCMe2CHMeN(2,6- Pr2i-C6H3)] intermediate in a two-step reduction. All products were characterized crystallographically.
    Original languageEnglish
    Pages (from-to)3792-3798
    Number of pages6
    JournalJournal of the Chemical Society, Dalton Transactions
    Issue number19
    DOIs
    Publication statusPublished - 7 Oct 2003

    Keywords

    • BETA-DIIMINE
    • {BETA-DIIMINE
    • {BOND
    • BORON-NITROGEN
    • BORON-NITROGEN} {BOND
    • CHEMISTRY
    • {CHEMISTRY
    • LIGANDS
    • complexes
    • {COMPLEXES
    • crystal
    • crystal structure
    • {CRYSTAL} {STRUCTURE
    • COMPLEXES
    • DERIVATIVES
    • REACTIVITY
    • {DERIVATIVES
    • MOLECULAR-STRUCTURE
    • {MOLECULAR-STRUCTURE
    • {REACTIVITY
    • SOLID-STATE
    • SOLID-STATE} {STRUCTURE
    • {SOLID-STATE} {STRUCTURE
    • BORON-NITROGEN BOND
    • {STRUCTURE

    Fingerprint

    Dive into the research topics of 'Borane and alane reductions of bulky N,N′-diaryl-1,3-diimines: Structural characterization of products and intermediates in the diastereoselective synthesis of 1,3-diamines'. Together they form a unique fingerprint.

    Cite this