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Synfacts 2010(8): 0947-0947  
DOI: 10.1055/s-0030-1257805
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Transacetalization

Contributor(s): Benjamin List, Olga Lifchits
I. Čorić, S. Vellalath, B. List*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

¡CoricŽ , Vellalath, and List developed an enantioselective intramolecular transacetalization using the catalytic Brønsted acid TRIP (2). Excellent control was achieved at low catalyst loading (1 mol%) for a broad range of substrates including a chiral racemic hydroxyacetal, which underwent a double kinetic resolution (product 3d). The bifunctional character of the phosphoric acid is speculated to selectively activate hydroxyacetals 1 through a hydrogen bond assembly, though the details of the exact mechanism are still unknown.