Synlett 2015; 26(18): 2473-2478
DOI: 10.1055/s-0034-1378882
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© Georg Thieme Verlag Stuttgart · New York

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

Chad A. Lewis*
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853, USA   Email: chad.lewis@cornell.edu
,
Matthew J. Moschitto
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853, USA   Email: chad.lewis@cornell.edu
,
David N. Vaccarello
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853, USA   Email: chad.lewis@cornell.edu
› Author Affiliations
Further Information

Publication History

Received: 23 June 2015

Accepted: 16 July 2015

Publication Date:
24 August 2015 (online)

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.

 
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