Allylic Oxide Regio-Resolution as a Tool for the Synthesis and Transfer of Carbasugars

Abstract

We report a method for the synthesis and transfer of carbasugars, a prevalent moiety throughout biology. This approach relies on the formation of diastereomeric π-allyl intermediates generated from racemic allylic oxide progenitors. Ligand directed nucleophilic attack occurs on the complexes resulting in enantioenriched regioisomers. This allowed for the generation of enantioenriched carbasugars from commodity chemicals. It is envisioned that by using the appropriate allylic oxide, ligand, and phenolic donor that any stereoarray of the carbasugars may be accessed and appended onto phenolic natural products.

Key words

total synthesis - asymmetric catalysis - glycosides - regioselectivity - natural products

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