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Free keywords:
EFFICIENT KINETIC RESOLUTION; FRUSTRATED LEWIS PAIRS;
B(C6F5)(3)-CATALYZED HYDROSILYLATION; ASYMMETRIC HYDROGENATION;
SELECTIVE DEOXYGENATION; SUGAR ALCOHOLS; ALKYL ETHERS; REDUCTION; DIOLS;
DEOXYDEHYDRATIONChemistry; boron; cyclic intermediates; deoxygenation; diols; silanes;
Abstract:
The selective deoxygenation of polyols is a frontier in our ability to harness the stereochemical and structural complexity of natural and synthetic feedstocks. Herein, we describe a highly active and selective boron-based catalytic system for the selective deoxygenation of terminal 1,2-diols at the primary position, a process that is enabled by the transient formation of a cyclic siloxane. The method provides an ideal complement to well-known catalytic asymmetric reactions to prepare synthetically challenging chiral 2-alkanols in nearly perfect enantiomeric excess, as illustrated in a short synthesis of the anti-inflammatory drug (R)-lisofylline.
