Chiral Phosphoric Acid Directed Regioselective Acetalization of Carbohydrate-Derived 1,2-Diols†
Dr. Enoch Mensah
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)
Search for more papers by this authorNicole Camasso
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)
Search for more papers by this authorWill Kaplan
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Pavel Nagorny
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)===Search for more papers by this authorDr. Enoch Mensah
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)
Search for more papers by this authorNicole Camasso
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)
Search for more papers by this authorWill Kaplan
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Pavel Nagorny
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)===Search for more papers by this authorWe are grateful to the University of Michigan for financial support.
Graphical Abstract
In control: A chiral phosphoric acid catalyst (see scheme) significantly enhances or completely overrides the inherent regioselective acetalization profiles exhibited by monosaccharide-derived 1,2-diol substrates. This study represents the first example of chiral-catalyst-directed regio- and enantioselective intermolecular acetalizations, which are complementary to existing methods for substrate-controlled functionalization of polyols.
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