Asymmetric bisboranes as bidentate catalysts for carbonyl substrates.
A new class of C(2) symmetric bisoxazaborolidinone compounds is described which exhibits bidentate binding to carbonyl substrates. Using the Diels-Alder reaction as a model system, the catalytic activity of these bis-Lewis acids is probed. Reaction rates and selectivities are observed that are higher than the corresponding mono-Lewis acids. This novel system offers a potentially powerful new approach to asymmetric Lewis acid catalysis.
Rodriguez
Andrew A
AA
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Zhao
Carrie
C
Shea
Kenneth J
KJ
D001880:Boranes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure
D001880:Boranes; D006573:Heterocyclic Compounds, 1-Ring; D007659:Ketones; D008024:Ligands; C527334:oxazaborolidinone