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Novel Bifunctional Chiral Brønsted Acid/Base Organocatalysis

V. N. Wakchaure, B. List

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Abstract

Significance A novel bifunctional chiral Brønsted acid/base catalyst is reported. The authors applied the new catalyst 1 to the enantioselective desymmetrization of meso -anhydrides, and the products were obtained in good yields and high enantioselectivities (er up to 99:1). The synthetic utility of this methodology was demonstrated in the symmetric formal synthesis of (+)-grandisol.

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What this paper is about

Significance A novel bifunctional chiral Brønsted acid/base catalyst is reported. The authors applied the new catalyst 1 to the enantioselective desymmetrization of meso -anhydrides, and the products were obtained in good yields and high enantioselectivities (er up to 99:1). The synthetic utility of this methodology was demonstrated in the symmetric formal synthesis of (+)-grandisol.

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Available abstract

Significance A novel bifunctional chiral Brønsted acid/base catalyst is reported. The authors applied the new catalyst 1 to the enantioselective desymmetrization of meso -anhydrides, and the products were obtained in good yields and high enantioselectivities (er up to 99:1). The synthetic utility of this methodology was demonstrated in the symmetric formal synthesis of (+)-grandisol.

Key concepts: Desymmetrization, Bifunctional, Chemistry, Enantioselective synthesis, Organocatalysis, Brønsted–Lowry acid–base theory, Catalysis, Base (topology)

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