Abstract
We developed a copper(I)-catalyzed diastereoselective incorporation of ketones into unprotected pyranoses. The reactivity was dependent on the bite angle of the diphosphine ligand in the copper catalyst, and we identified an achiral diphosphine ligand L1 bearing an exceptionally large bite angle as the optimal ligand. A copper(I)-conjugated Brϕnsted base catalyst containing ligand L1 enabled the C–C bond-forming reaction via in situ-generated copper(I) enolate, even in the presence of multiple unprotected hydroxy groups. A variety of ketones were introduced with high diastereoselectivity. The product 2,6-cis-pyrans has many applications for the synthesis of biologically active molecules.
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