A New Structural Motif for Bifunctional Brønsted Acid/Base Organocatalysis

Wakchaure, Vijay N.; List, Benjamin

doi:10.1002/anie.201000637

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A New Structural Motif for Bifunctional Brønsted Acid/Base Organocatalysis

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Wakchaure, Vijay N.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Wakchaure, V. N., & List, B. (2010). A New Structural Motif for Bifunctional Brønsted Acid/Base Organocatalysis. Angewandte Chemie International Edition, 49(24), 4136-4139. doi:10.1002/anie.201000637.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-8D93-5

Abstract

Naturally synthetic: Acid/base catalyst (S)‐1 can be used in highly enantioselective alcoholytic desymmetrizations of meso anhydrides. For example, the methanolysis of cyclobutane anhydride derivative 2 gave hemiester 3 in 99:1 e.r. (see scheme). Ester 3 was used in a short enantioselective synthesis of (+)‐grandisol.